US8263679B2 - Prepolymers with dangling polysiloxane-containing polymer chains - Google Patents
Prepolymers with dangling polysiloxane-containing polymer chains Download PDFInfo
- Publication number
- US8263679B2 US8263679B2 US13/284,092 US201113284092A US8263679B2 US 8263679 B2 US8263679 B2 US 8263679B2 US 201113284092 A US201113284092 A US 201113284092A US 8263679 B2 US8263679 B2 US 8263679B2
- Authority
- US
- United States
- Prior art keywords
- polysiloxane
- lens
- group
- contact lens
- trimethylsiloxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- -1 polysiloxane Polymers 0.000 title claims abstract description 151
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 134
- 229920000642 polymer Polymers 0.000 title abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 69
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 48
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 48
- 239000001301 oxygen Substances 0.000 claims abstract description 48
- 239000000017 hydrogel Substances 0.000 claims abstract description 32
- 230000035699 permeability Effects 0.000 claims abstract description 25
- 230000010220 ion permeability Effects 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims description 121
- 125000002348 vinylic group Chemical group 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 46
- 239000004971 Cross linker Substances 0.000 claims description 40
- 229920001577 copolymer Polymers 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 230000002209 hydrophobic effect Effects 0.000 claims description 25
- 125000000524 functional group Chemical group 0.000 claims description 23
- 238000004132 cross linking Methods 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 10
- 239000012986 chain transfer agent Substances 0.000 claims description 9
- 238000001723 curing Methods 0.000 claims description 9
- 238000009792 diffusion process Methods 0.000 claims description 9
- 238000000108 ultra-filtration Methods 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 238000007334 copolymerization reaction Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 150000003141 primary amines Chemical class 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 150000003512 tertiary amines Chemical group 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 4
- IHNDNMHBSSSIPV-UHFFFAOYSA-N 2-methyl-n-[3-tris(trimethylsilyloxy)silylpropyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C IHNDNMHBSSSIPV-UHFFFAOYSA-N 0.000 claims description 4
- LUTFTISESXWDHG-UHFFFAOYSA-N 3-aminopropyl 2-methylprop-2-enoate;hydrochloride Chemical compound Cl.CC(=C)C(=O)OCCCN LUTFTISESXWDHG-UHFFFAOYSA-N 0.000 claims description 4
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 3
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 3
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical group CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 3
- VJUBAEVLVNBCON-UHFFFAOYSA-N n-[3-tris(trimethylsilyloxy)silylpropyl]prop-2-enamide Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCNC(=O)C=C VJUBAEVLVNBCON-UHFFFAOYSA-N 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 2
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 2
- NPPNUGUVBUJRAB-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxyethyl ethenyl carbonate Chemical compound CC(C)(C)[Si](C)(C)OCCOC(=O)OC=C NPPNUGUVBUJRAB-UHFFFAOYSA-N 0.000 claims description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims description 2
- ZIFLDVXQTMSDJE-UHFFFAOYSA-N 3-[[dimethyl-[3-(2-methylprop-2-enoyloxy)propyl]silyl]oxy-dimethylsilyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)CCCOC(=O)C(C)=C ZIFLDVXQTMSDJE-UHFFFAOYSA-N 0.000 claims description 2
- NWBTXZPDTSKZJU-UHFFFAOYSA-N 3-[dimethyl(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)C NWBTXZPDTSKZJU-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- LVGSUQNJVOIUIW-UHFFFAOYSA-N 5-(dimethylamino)-2-methylpent-2-enamide Chemical compound CN(C)CCC=C(C)C(N)=O LVGSUQNJVOIUIW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001774 Perfluoroether Polymers 0.000 claims description 2
- PKDAKIZIHVXQTQ-UHFFFAOYSA-N [2-hydroxy-3-[3-tris(trimethylsilyloxy)silylpropoxy]propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C PKDAKIZIHVXQTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000000502 dialysis Methods 0.000 claims description 2
- KZJNAICCMJTRKF-UHFFFAOYSA-N ethenyl 2-trimethylsilylethyl carbonate Chemical compound C[Si](C)(C)CCOC(=O)OC=C KZJNAICCMJTRKF-UHFFFAOYSA-N 0.000 claims description 2
- NDXTZJDCEOXFOP-UHFFFAOYSA-N ethenyl 3-tris(trimethylsilyloxy)silylpropyl carbonate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCOC(=O)OC=C NDXTZJDCEOXFOP-UHFFFAOYSA-N 0.000 claims description 2
- BHBDVHVTNOYHLK-UHFFFAOYSA-N ethenyl 3-tris(trimethylsilyloxy)silylpropylsulfanylformate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCSC(=O)OC=C BHBDVHVTNOYHLK-UHFFFAOYSA-N 0.000 claims description 2
- ILHMPZFVDISGNP-UHFFFAOYSA-N ethenyl n-[3-tris(trimethylsilyloxy)silylpropyl]carbamate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCNC(=O)OC=C ILHMPZFVDISGNP-UHFFFAOYSA-N 0.000 claims description 2
- KRAZQXAPJAYYJI-UHFFFAOYSA-N ethenyl trimethylsilylmethyl carbonate Chemical compound C[Si](C)(C)COC(=O)OC=C KRAZQXAPJAYYJI-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 125000001153 fluoro group Chemical class F* 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 2
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 2
- KYKIFKUTBWKKRE-UHFFFAOYSA-N n-ethenylpropan-2-amine Chemical compound CC(C)NC=C KYKIFKUTBWKKRE-UHFFFAOYSA-N 0.000 claims description 2
- DRNXZGJGRSUXHW-UHFFFAOYSA-N silyl carbamate Chemical compound NC(=O)O[SiH3] DRNXZGJGRSUXHW-UHFFFAOYSA-N 0.000 claims description 2
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 claims 1
- HVOZRYQITRPMRO-UHFFFAOYSA-N [3-[bis(trimethylsilyloxy)methyl-propylsilyl]oxy-2-hydroxypropyl] 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCC(CO[SiH](C(O[Si](C)(C)C)O[Si](C)(C)C)CCC)O HVOZRYQITRPMRO-UHFFFAOYSA-N 0.000 claims 1
- RWEUKWCZWYHIQA-UHFFFAOYSA-N ethenyl 3-trimethylsilylpropyl carbonate Chemical compound C[Si](C)(C)CCCOC(=O)OC=C RWEUKWCZWYHIQA-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 36
- 230000002829 reductive effect Effects 0.000 abstract description 7
- 239000000243 solution Substances 0.000 description 20
- 238000000465 moulding Methods 0.000 description 18
- 239000003999 initiator Substances 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 14
- 230000005855 radiation Effects 0.000 description 14
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 13
- 230000008569 process Effects 0.000 description 13
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 12
- 230000000845 anti-microbial effect Effects 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 210000004087 cornea Anatomy 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 238000013461 design Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- 229920000831 ionic polymer Polymers 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 5
- 239000002082 metal nanoparticle Substances 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000004381 surface treatment Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 0 C.C.[1*][Si]([2*])(C)OC Chemical compound C.C.[1*][Si]([2*])(C)OC 0.000 description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 4
- 239000004713 Cyclic olefin copolymer Substances 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012867 bioactive agent Substances 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229920001477 hydrophilic polymer Polymers 0.000 description 4
- 239000002105 nanoparticle Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical group ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229960003328 benzoyl peroxide Drugs 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000004438 eyesight Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 239000012633 leachable Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical group CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 2
- LPCWIFPJLFCXRS-UHFFFAOYSA-N 1-ethylcyclopentan-1-ol Chemical compound CCC1(O)CCCC1 LPCWIFPJLFCXRS-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 2
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 2
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
- NGDNVOAEIVQRFH-UHFFFAOYSA-N 2-nonanol Chemical compound CCCCCCCC(C)O NGDNVOAEIVQRFH-UHFFFAOYSA-N 0.000 description 2
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- PQOSNJHBSNZITJ-UHFFFAOYSA-N 3-methyl-3-heptanol Chemical compound CCCCC(C)(O)CC PQOSNJHBSNZITJ-UHFFFAOYSA-N 0.000 description 2
- JEWXYDDSLPIBBO-UHFFFAOYSA-N 3-methyl-3-octanol Chemical compound CCCCCC(C)(O)CC JEWXYDDSLPIBBO-UHFFFAOYSA-N 0.000 description 2
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 2
- ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 2
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- HLJYBXJFKDDIBI-UHFFFAOYSA-N O=[PH2]C(=O)C1=CC=CC=C1 Chemical compound O=[PH2]C(=O)C1=CC=CC=C1 HLJYBXJFKDDIBI-UHFFFAOYSA-N 0.000 description 2
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 2
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 235000013980 iron oxide Nutrition 0.000 description 2
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 229960004958 ketotifen Drugs 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical group CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical group CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 2
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910052594 sapphire Inorganic materials 0.000 description 2
- 239000010980 sapphire Substances 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- ZQTYQMYDIHMKQB-RRKCRQDMSA-N (1s,3r,4r)-bicyclo[2.2.1]heptan-3-ol Chemical compound C1C[C@H]2[C@H](O)C[C@@H]1C2 ZQTYQMYDIHMKQB-RRKCRQDMSA-N 0.000 description 1
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 1
- LCPUCXXYIYXLJY-UHFFFAOYSA-N 1,1,2,4,4,4-hexafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)C(F)CC(F)(F)F LCPUCXXYIYXLJY-UHFFFAOYSA-N 0.000 description 1
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- LAVARTIQQDZFNT-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-yl acetate Chemical compound COCC(C)OCC(C)OC(C)=O LAVARTIQQDZFNT-UHFFFAOYSA-N 0.000 description 1
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical compound CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- JNOZGFXJZQXOSU-UHFFFAOYSA-N 1-chloro-2-methylpropan-2-ol Chemical compound CC(C)(O)CCl JNOZGFXJZQXOSU-UHFFFAOYSA-N 0.000 description 1
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 1
- LVJZCPNIJXVIAT-UHFFFAOYSA-N 1-ethenyl-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(C=C)C(F)=C1F LVJZCPNIJXVIAT-UHFFFAOYSA-N 0.000 description 1
- CTXUTPWZJZHRJC-UHFFFAOYSA-N 1-ethenylpyrrole Chemical compound C=CN1C=CC=C1 CTXUTPWZJZHRJC-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- AUYBPOVOWOLZJF-UHFFFAOYSA-N 1-methoxy-2-(2-methoxypropoxy)propane;1-phenoxypropan-2-ol Chemical compound COCC(C)OCC(C)OC.CC(O)COC1=CC=CC=C1 AUYBPOVOWOLZJF-UHFFFAOYSA-N 0.000 description 1
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 description 1
- QIGOESOMEANKQI-UHFFFAOYSA-N 1-methylcyclopentane-1,3-diol Chemical compound CC1(O)CCC(O)C1 QIGOESOMEANKQI-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 1
- PLSMHHUFDLYURK-UHFFFAOYSA-N 2,3,4-trimethyl-3-pentanol Chemical compound CC(C)C(C)(O)C(C)C PLSMHHUFDLYURK-UHFFFAOYSA-N 0.000 description 1
- IKECULIHBUCAKR-UHFFFAOYSA-N 2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(C)O IKECULIHBUCAKR-UHFFFAOYSA-N 0.000 description 1
- FMLSQAUAAGVTJO-UHFFFAOYSA-N 2,4-dimethylpentan-2-ol Chemical compound CC(C)CC(C)(C)O FMLSQAUAAGVTJO-UHFFFAOYSA-N 0.000 description 1
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- ACUZDYFTRHEKOS-SNVBAGLBSA-N 2-Decanol Natural products CCCCCCCC[C@@H](C)O ACUZDYFTRHEKOS-SNVBAGLBSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 1
- AOUSBQVEVZBMNI-UHFFFAOYSA-N 2-bromoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCBr AOUSBQVEVZBMNI-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 1
- BQBSIHIZDSHADD-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1,3-oxazole Chemical compound C=CC1=NCCO1 BQBSIHIZDSHADD-UHFFFAOYSA-N 0.000 description 1
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 1
- WTXBAYPZJKPZHX-UHFFFAOYSA-N 2-methyldecan-2-ol Chemical compound CCCCCCCCC(C)(C)O WTXBAYPZJKPZHX-UHFFFAOYSA-N 0.000 description 1
- ACBMYYVZWKYLIP-UHFFFAOYSA-N 2-methylheptan-2-ol Chemical compound CCCCCC(C)(C)O ACBMYYVZWKYLIP-UHFFFAOYSA-N 0.000 description 1
- KRIMXCDMVRMCTC-UHFFFAOYSA-N 2-methylhexan-2-ol Chemical compound CCCCC(C)(C)O KRIMXCDMVRMCTC-UHFFFAOYSA-N 0.000 description 1
- KBCNUEXDHWDIFX-UHFFFAOYSA-N 2-methyloctan-2-ol Chemical compound CCCCCCC(C)(C)O KBCNUEXDHWDIFX-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- XGLHYBVJPSZXIF-UHFFFAOYSA-N 2-phenylbutan-2-ol Chemical compound CCC(C)(O)C1=CC=CC=C1 XGLHYBVJPSZXIF-UHFFFAOYSA-N 0.000 description 1
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- NMRPBPVERJPACX-QMMMGPOBSA-N 3-Octanol Natural products CCCCC[C@@H](O)CC NMRPBPVERJPACX-QMMMGPOBSA-N 0.000 description 1
- WNDLTOTUHMHNOC-UHFFFAOYSA-N 3-ethylhexan-3-ol Chemical compound CCCC(O)(CC)CC WNDLTOTUHMHNOC-UHFFFAOYSA-N 0.000 description 1
- XKIRHOWVQWCYBT-UHFFFAOYSA-N 3-ethylpentan-3-ol Chemical compound CCC(O)(CC)CC XKIRHOWVQWCYBT-UHFFFAOYSA-N 0.000 description 1
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 1
- KYWJZCSJMOILIZ-UHFFFAOYSA-N 3-methylhexan-3-ol Chemical compound CCCC(C)(O)CC KYWJZCSJMOILIZ-UHFFFAOYSA-N 0.000 description 1
- VZBFPIMCUSPDLS-UHFFFAOYSA-N 3-methylnonan-3-ol Chemical compound CCCCCCC(C)(O)CC VZBFPIMCUSPDLS-UHFFFAOYSA-N 0.000 description 1
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- GNROHGFUVTWFNG-UHFFFAOYSA-N 4-ethylheptan-4-ol Chemical compound CCCC(O)(CC)CCC GNROHGFUVTWFNG-UHFFFAOYSA-N 0.000 description 1
- IQXKGRKRIRMQCQ-UHFFFAOYSA-N 4-methylheptan-4-ol Chemical compound CCCC(C)(O)CCC IQXKGRKRIRMQCQ-UHFFFAOYSA-N 0.000 description 1
- GDCOAKPWVJCNGI-UHFFFAOYSA-N 4-methylnonan-4-ol Chemical compound CCCCCC(C)(O)CCC GDCOAKPWVJCNGI-UHFFFAOYSA-N 0.000 description 1
- RXSIKQJQLQRQQY-UHFFFAOYSA-N 4-methyloctan-4-ol Chemical compound CCCCC(C)(O)CCC RXSIKQJQLQRQQY-UHFFFAOYSA-N 0.000 description 1
- OHSMKBPEDBXYDU-UHFFFAOYSA-N 4-propan-2-ylheptan-4-ol Chemical compound CCCC(O)(C(C)C)CCC OHSMKBPEDBXYDU-UHFFFAOYSA-N 0.000 description 1
- SJTPBRMACCDJPZ-UHFFFAOYSA-N 4-propylheptan-4-ol Chemical compound CCCC(O)(CCC)CCC SJTPBRMACCDJPZ-UHFFFAOYSA-N 0.000 description 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 1
- NIXVAPHNPNMUIX-UHFFFAOYSA-N 6-amino-2-methylhex-2-enamide Chemical compound NC(=O)C(C)=CCCCN NIXVAPHNPNMUIX-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101150055539 HADH gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QQILFGKZUJYXGS-UHFFFAOYSA-N Indigo dye Chemical compound C1=CC=C2C(=O)C(C3=C(C4=CC=CC=C4N3)O)=NC2=C1 QQILFGKZUJYXGS-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- BWYMWCLNVMZZHL-UHFFFAOYSA-N N-[3-silyl-1,3,3-tris(trimethylsilyloxy)propyl]prop-2-enamide Chemical compound C=CC(=O)NC(O[Si](C)(C)C)CC([SiH3])(O[Si](C)(C)C)O[Si](C)(C)C BWYMWCLNVMZZHL-UHFFFAOYSA-N 0.000 description 1
- NFFRLZCGHFMGEP-UHFFFAOYSA-N OC(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)=C(C(C(N(F)F)(F)F)(F)F)C(C(C(F)(F)F)(F)F)=S)=O Chemical compound OC(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)=C(C(C(N(F)F)(F)F)(F)F)C(C(C(F)(F)F)(F)F)=S)=O NFFRLZCGHFMGEP-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ALLWOAVDORUJLA-UHFFFAOYSA-N Rebamipida Chemical compound C=1C(=O)NC2=CC=CC=C2C=1CC(C(=O)O)NC(=O)C1=CC=C(Cl)C=C1 ALLWOAVDORUJLA-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- WNMRZSPHABTZPY-UHFFFAOYSA-N [3-[3-[bis(trimethylsilyloxy)methylsilyl]propoxy]-2-hydroxypropyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COCCC[SiH2]C(O[Si](C)(C)C)O[Si](C)(C)C WNMRZSPHABTZPY-UHFFFAOYSA-N 0.000 description 1
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229920006187 aquazol Polymers 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000002801 charged material Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 229940096890 d&c violet no. 2 Drugs 0.000 description 1
- ACUZDYFTRHEKOS-UHFFFAOYSA-N decan-2-ol Chemical compound CCCCCCCCC(C)O ACUZDYFTRHEKOS-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- BLZSRIYYOIZLJL-UHFFFAOYSA-N ethenyl pentanoate Chemical compound CCCCC(=O)OC=C BLZSRIYYOIZLJL-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- UJOLYBGCVQJVLI-UHFFFAOYSA-N ethenyl propyl carbonate Chemical compound CCCOC(=O)OC=C UJOLYBGCVQJVLI-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- ZQTYQMYDIHMKQB-UHFFFAOYSA-N exo-norborneol Chemical compound C1CC2C(O)CC1C2 ZQTYQMYDIHMKQB-UHFFFAOYSA-N 0.000 description 1
- 210000000887 face Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000012209 glucono delta-lactone Nutrition 0.000 description 1
- 229960003681 gluconolactone Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 229920001480 hydrophilic copolymer Polymers 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000037427 ion transport Effects 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229940091853 isobornyl acrylate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- ZCGOMHNNNFPNMX-KYTRFIICSA-N levocabastine Chemical compound C1([C@@]2(C(O)=O)CCN(C[C@H]2C)[C@@H]2CC[C@@](CC2)(C#N)C=2C=CC(F)=CC=2)=CC=CC=C1 ZCGOMHNNNFPNMX-KYTRFIICSA-N 0.000 description 1
- 229960001120 levocabastine Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229960004305 lodoxamide Drugs 0.000 description 1
- RVGLGHVJXCETIO-UHFFFAOYSA-N lodoxamide Chemical compound OC(=O)C(=O)NC1=CC(C#N)=CC(NC(=O)C(O)=O)=C1Cl RVGLGHVJXCETIO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 229960004398 nedocromil Drugs 0.000 description 1
- RQTOOFIXOKYGAN-UHFFFAOYSA-N nedocromil Chemical compound CCN1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1OC(C(O)=O)=CC(=O)C1=C2 RQTOOFIXOKYGAN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- FZGSCNQUWMMDIG-UHFFFAOYSA-N phenyl(phosphanyl)methanone Chemical compound PC(=O)C1=CC=CC=C1 FZGSCNQUWMMDIG-UHFFFAOYSA-N 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 125000005541 phosphonamide group Chemical group 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229950004535 rebamipide Drugs 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 235000019756 total sulphur amino acid Nutrition 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
- C08L51/085—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds on to polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
Definitions
- the present invention is related to a class of silicone-containing prepolymers with dangling polysiloxane-containing polymer chains and uses thereof.
- the present invention is related to silicone hydrogel contact lenses made from this class of silicone-containing prepolymers.
- soft silicone hydrogel contact lenses has become popular because of their high oxygen permeability and comfort.
- Soft contact lenses conform closely to the shape of the eye, so oxygen cannot easily circumvent the lens.
- Soft contact lenses must allow oxygen from the surrounding air (i.e., oxygen) to reach the cornea because the cornea does not receive oxygen from the blood supply like other tissue. If sufficient oxygen does not reach the cornea, corneal swelling occurs. Extended periods of oxygen deprivation cause the undesirable growth of blood vessels in the cornea.
- a silicone hydrogel contact lens allows sufficient oxygen to permeate through the lens to the cornea and to have minimal adverse effects on corneal health.
- the present invention in one aspect, provides an actinically crosslinkable prepolymer.
- the prepolymer of the invention comprises: (1) dangling polysiloxane units derived from one or more monoethylenically functionalized polysiloxane-containing monomers and/or one or more monoethylenically-functionalized polysiloxane-containing macromers, wherein the dangling polysiloxane units is free of ethylenically unsaturated group; (2) hydrophilic units derived from one or more hydrophilic vinylic monomers; (3) crosslinking units derived from at least one polysiloxane-containing crosslinker and/or at least one silicone-free crosslinker; and (4) optionally hydrophobic units derived from at least one hydrophobic vinylic monomer, wherein the prepolymer comprises multiple ethylenically unsaturated groups and is capable of being actinically crosslinked, in the absence of one or more monomers, to form a silicone hydrogel material.
- the invention provides a soft contact lens.
- the soft contact lens of the invention comprises: a silicone hydrogel material that is obtained by curing a lens-forming material in a mold, wherein the lens-forming material comprises an actinically crosslinkable prepolymer and is substantially free of vinylic monomers and crosslinking agent with molecular weight of less than 1500 Daltons, wherein the prepolymer comprises (1) dangling polysiloxane units derived from one or more monoethylenically functionalized polysiloxane-containing monomers and/or one or more monoethylenically-functionalized polysiloxane-containing macromers, wherein the dangling polysiloxane units is free of ethylenically unsaturated groups; (2) hydrophilic units derived from one or more hydrophilic vinylic monomers; (3) crosslinking units derived from at least one polysiloxane-containing crosslinker and/or at least one silicone-free crosslinker; (4) multiple ethylenically
- the invention provides a method for producing soft contact lenses.
- the method comprises the steps of: providing a mold for making a soft contact lens, wherein the mold has a first mold half with a first molding surface defining the anterior surface of a contact lens and a second mold half with a second molding surface defining the posterior surface of the contact lens, wherein said first and second mold halves are configured to receive each other such that a cavity is formed between said first and second molding surfaces; introduce a lens-forming material into the cavity, wherein the lens-forming material comprises one or more actinically crosslinkable prepolymers and is substantially free of vinylic monomer and/or crosslinking agent with molecular weight less than 1500 Daltons, wherein each of said one or more prepolymers comprises (1) dangling polysiloxane units derived from one or more monoethylenically functionalized polysiloxane-containing monomers and/or one or more monoethylenically-functionalized polysiloxane-containing macromers, wherein the
- an “ophthalmic device”, as used herein, refers to a contact lens (hard or soft), an intraocular lens, a corneal onlay, other ophthalmic devices (e.g., stents, glaucoma shunt, or the like) used on or about the eye or ocular vicinity.
- a contact lens hard or soft
- an intraocular lens e.g., an intraocular lens
- a corneal onlay e.g., stents, glaucoma shunt, or the like
- Contact Lens refers to a structure that can be placed on or within a wearer's eye.
- a contact lens can correct, improve, or alter a user's eyesight, but that need not be the case.
- a contact lens can be of any appropriate material known in the art or later developed, and can be a soft lens, a hard lens, or a hybrid lens.
- a “silicone hydrogel contact lens” refers to a contact lens comprising a silicone hydrogel material.
- hydrogel or “hydrogel material” refers to a polymeric material which can absorb at least 10 percent by weight of water when it is fully hydrated.
- a “silicone hydrogel” refers to a silicone-containing hydrogel obtained by copolymerization of a polymerizable composition comprising at least one silicone-containing monomer or at least one silicone-containing macromer or at least one crosslinkable silicone-containing prepolymer.
- Hydrophilic describes a material or portion thereof that will more readily associate with water than with lipids.
- a “monomer” means a low molecular weight compound that can be polymerized. Low molecular weight typically means average molecular weights less than 700 Daltons.
- a “macromer” refers to a medium and high molecular weight compound which can be polymerized and/or crosslinked.
- Medium and high molecular weight typically means average molecular weights greater than 700 Daltons.
- polysiloxane refers to a moiety of
- R 1 and R 2 are independently a monovalent C 1 -C 10 alkyl, C 1 -C 10 ether, C 1 -C 10 fluoroalkyl, C 1 -C 10 fluoroether, or C 6 -C 18 aryl radical, which may comprise hydroxy group, primary, secondary, or tertiary amine group, carboxy group, or carboxylic acid; n is an integer of 4 or higher.
- a “vinylic monomer”, as used herein, refers to a monomer that has only one ethylenically unsaturated group and can be polymerized actinically or thermally.
- olefinically unsaturated group or “ethylenically unsaturated group” is employed herein in a broad sense and is intended to encompass any groups containing a >C ⁇ C ⁇ group.
- exemplary ethylenically unsaturated groups include without limitation acryloyl, methacryloyl, allyl, vinyl, styrenyl, or other C ⁇ C containing groups.
- actinically in reference to curing, crosslinking or polymerizing of a polymerizable composition, a prepolymer or a material means that the curing (e.g., crosslinked and/or polymerized) is performed by actinic irradiation, such as, for example, UV irradiation, ionized radiation (e.g. gamma ray or X-ray irradiation), microwave irradiation, and the like.
- actinic irradiation such as, for example, UV irradiation, ionized radiation (e.g. gamma ray or X-ray irradiation), microwave irradiation, and the like.
- fluid indicates that a material is capable of flowing like a liquid.
- a “hydrophilic vinylic monomer” refers to a vinylic monomer which can be polymerized to form a polymer that is water-soluble or can absorb at least 10 percent by weight of water when fully hydrated.
- hydrophobic vinylic monomer refers to a vinylic monomer which is polymerized to form a polymer that is insoluble in water and can absorb less than 10 percent by weight water when fully hydrated.
- a “prepolymer” refers to a starting polymer which contains multiple ethylenically unsaturated groups and can be cured (e.g., crosslinked) actinically to obtain a crosslinked polymer (i.e., final polymer) having a molecular weight much higher than the starting polymer.
- Multiple ethylenically unsaturated groups means at least two, preferably at least three ethylenically unsaturated groups.
- a “silicone-containing prepolymer” refers to a prepolymer which contains silicone and ethylenically unsaturated groups can be crosslinked actinically to obtain a crosslinked polymer having a molecular weight much higher than the starting polymer.
- Molecular weight of a polymeric material refers to the number-average molecular weight unless otherwise specifically noted or unless testing conditions indicate otherwise.
- Polymer means a material formed by polymerizing one or more monomers.
- ethylenically functionalize in reference to a copolymer is intended to describe that one or more ethylenically unsaturated groups have been covalently attached to a copolymer through the pendant or terminal functional groups of the copolymer according to a coupling process.
- a “monoethylenically functionalized” in reference to a compound means that the compound has been modified chemically to contain one single ethylenically unsaturated group.
- a “diethylenically functionalized” a compound means that the compound has been modified chemically to contain only two ethylenically unsaturated groups.
- dangling polysiloxane units of a prepolymer is intended to refer to the units each comprise a polysiloxane-containing polymer chain which is anchored to the main chain of the prepolymer through one single covalent linkage (preferably at one of the ends of the polysiloxane-containing polymer chain).
- a “photoinitiator” refers to a chemical that initiates radical crosslinking/polymerizing reaction by the use of light.
- Suitable photoinitiators include, without limitation, benzoin methyl ether, diethoxyacetophenone, a benzoylphosphine oxide, 1-hydroxycyclohexyl phenyl ketone, Darocure® types, and Irgacure® types, preferably Darocure® 1173, and Irgacure® 2959.
- thermal initiator refers to a chemical that initiates radical crosslinking/polymerizing reaction by the use of heat energy.
- suitable thermal initiators include, but are not limited to, 2,2′-azobis(2,4-dimethylpentanenitrile), 2,2′-azobis(2-methylpropanenitrile), 2,2′-azobis(2-methylbutanenitrile), peroxides such as benzoyl peroxide, and the like.
- the thermal initiator is 2,2′-azobis(isobutyronitrile) (AIBN).
- a “spatial limitation of actinic radiation” refers to an act or process in which energy radiation in the form of rays is directed by, for example, a mask or screen or combinations thereof, to impinge, in a spatially restricted manner, onto an area having a well defined peripheral boundary.
- a spatial limitation of UV radiation can be achieved by using a mask or screen that has a transparent or open region (unmasked region) surrounded by a UV impermeable region (masked region), as schematically illustrated in FIGS. 1-9 of U.S. Pat. No. 6,627,124 (herein incorporated by reference in its entirety).
- the unmasked region has a well defined peripheral boundary with the unmasked region.
- the energy used for the crosslinking is radiation energy, especially UV radiation, gamma radiation, electron radiation or thermal radiation, the radiation energy preferably being in the form of a substantially parallel beam in order on the one hand to achieve good restriction and on the other hand efficient use of the energy.
- “Visibility tinting” in reference to a lens means dying (or coloring) of a lens to enable the user to easily locate a lens in a clear solution within a lens storage, disinfecting or cleaning container. It is well known in the art that a dye and/or a pigment can be used in visibility tinting a lens.
- Dyes means a substance that is soluble in a solvent and that is used to impart color. Dyes are typically translucent and absorb but do not scatter light. Any suitable biocompatible dye can be used in the present invention.
- a “Pigment” means a powdered substance that is suspended in a liquid in which it is insoluble.
- a pigment can be a fluorescent pigment, phosphorescent pigment, pearlescent pigment, or conventional pigment. While any suitable pigment may be employed, it is presently preferred that the pigment be heat resistant, non-toxic and insoluble in aqueous solutions.
- “Surface modification”, as used herein, means that an article has been treated in a surface treatment process (or a surface modification process) prior to or posterior to the formation of the article, in which (1) a coating is applied to the surface of the article, (2) chemical species are adsorbed onto the surface of the article, (3) the chemical nature (e.g., electrostatic charge) of chemical groups on the surface of the article are altered, or (4) the surface properties of the article are otherwise modified.
- Exemplary surface treatment processes include, but are not limited to, plasma processes in which an ionized gas is applied to the surface of an article (see, for example, U.S. Pat. Nos.
- the plasma gas is preferably a mixture of lower alkanes and nitrogen, oxygen or an inert gas.
- LbL coating refers to a coating that is not covalently attached to a contact lens or a mold half and is obtained through a layer-by-layer (“LbL”) deposition of polyionic (or charged) and/or non-charged materials on the lens or mold half.
- An LbL coating can be composed of one or more layers.
- a “polyionic material” refers to a polymeric material that has a plurality of charged groups or ionizable groups, such as polyelectrolytes, p- and n-type doped conducting polymers.
- Polyionic materials include both polycationic (having positive charges) and polyanionic (having negative charges) materials.
- Formation of an LbL coating on a contact lens or mold half may be accomplished in a number of ways, for example, as described in U.S. Pat. Nos. 6,451,871, 6,719,929, 6,793,973, 6,811,805, 6,896,926 (herein incorporated by references in their entirety).
- an “antimicrobial agent”, as used herein, refers to a chemical that is capable of decreasing or eliminating or inhibiting the growth of microorganisms such as that term is known in the art.
- Antimicrobial metals are metals whose ions have an antimicrobial effect and which are biocompatible.
- Preferred antimicrobial metals include Ag, Au, Pt, Pd, Ir, Sn, Cu, Sb, Bi and Zn, with Ag being most preferred.
- Antimicrobial metal-containing nanoparticles refer to particles having a size of less than 1 micrometer and containing at least one antimicrobial metal present in one or more of its oxidation states.
- Antimicrobial metal nanoparticles refer to particles which is made essentially of an antimicrobial metal and have a size of less than 1 micrometer.
- the antimicrobial metal in the antimicrobial metal nanoparticles can be present in one or more of its oxidation states.
- silver-containing nanoparticles can contain silver in one or more of its oxidation states, such as Ag 0 , Ag 1+ , and Ag 2+ .
- Stabilized antimicrobial metal nanoparticles refer to antimicrobial metal nanoparticles which are stabilized by a stabilizer during their preparation. Stabilized antimicrobial metal nano-particles can be either positively charged or negatively charged or neutral, largely depending on a material (or so-called stabilizer) which is present in a solution for preparing the nano-particles and can stabilize the resultant nano-particles.
- a stabilizer can be any known suitable material. Exemplary stabilizers include, without limitation, positively charged polyionic materials, negatively charged polyionic materials, polymers, surfactants, salicylic acid, alcohols and the like.
- oxygen transmissibility of a lens is the rate at which oxygen will pass through a specific ophthalmic lens.
- Oxygen transmissibility, Dk/t is conventionally expressed in units of barrers/mm, where t is the average thickness of the material [in units of mm] over the area being measured and “barrer/mm” is defined as: [(cm 3 oxygen)/(cm 2 )(sec)(mm 2 Hg)] ⁇ 10 ⁇ 9
- Intrinsic oxygen permeability is the rate at which oxygen will pass through a material. Oxygen permeability is conventionally expressed in units of barrers, where “barrer” is defined as: [(cm 3 oxygen)(mm)/(cm 2 )(sec)(mm 2 Hg)] ⁇ 10 ⁇ 10
- a lens having a Dk of 90 barrers (“oxygen permeability barrers”) and a thickness of 90 microns (0.090 mm) would have a Dk/t of
- a high oxygen permeability in reference to a material or a contact lens characterized by apparent oxygen permeability of at least 40 barrers or larger measured with a sample (film or lens) of 100 microns in thickness according to a coulometric method described in Examples.
- the “ion permeability” through a lens correlates with both the Ionoflux Diffusion Coefficient and the Ionoton Ion Permeability Coefficient.
- A area of lens exposed [mm 2 ]
- C(0) initial concentration of sodium ions in donor cell
- A membrane area, i.e., lens area exposed to cells
- V volume of cell compartment (3.0 ml)
- d average lens thickness in the area exposed
- An Ionoflux Diffusion Coefficient, D of greater than about 1.5 ⁇ 10 ⁇ 6 mm 2 /min is preferred, while greater than about 2.6 ⁇ 10 ⁇ 6 mm 2 /min is more preferred and greater than about 6.4 ⁇ 10 ⁇ 6 mm 2 /min is most preferred.
- Ion permeability is one of the predictors of on-eye movement, because the permeability of ions is believed to be directly proportional to the permeability of water.
- a “reduced E modulus” or “reduced modulus” or “reduced Young's modulus” in reference to a testing silicone hydrogel lens obtained by crosslinking a first prepolymer with dangling polysiloxane polymer chains is intended to describe that the E modulus (or modulus) of the lens is smaller than a control lens obtained from a second prepolymer without dangling polysiloxane polymer chains but having substantially identical amount (by weight) of polysiloxane (based on compositions for making both the first and second prepolymers).
- a “reduction in modulus ( ⁇ E)” of a lens is calculated based on the following formula
- IP IP - IP control IP control ⁇ 100 ⁇ % in which IP is the ion permeability of a testing lens obtained from a first prepolymer with dangling polysiloxane polymer chains and IP control is the ion permeability of a control lens obtained from a second prepolymer without dangling polysiloxane polymer chains but having substantially identical amount (by weight) of polysiloxane (based on the compositions for making both the first and second prepolymers) as shown in Example 2.
- the invention is directed to a class of actinically crosslinkable silicone-containing prepolymers. It is partly based on discovery that by incorporating dangling polysiloxane polymer chains into an actinically crosslinkable silicone-containing prepolymer, such prepolymer can be used to produce silicone hydrogel contact lenses having a reduced E modulus and substantially equivalent oxygen permeability. The ion permeability of the resultant lenses can be enhanced by incorporating dangling polysiloxane polymer chains.
- Such prepolymers can be used to prepare silicone hydrogel contact lenses, in particularly according to the Lightstream TechnologyTM (CIBA Vision).
- the present invention in one aspect, provides an actinically crosslinkable prepolymer.
- the prepolymer of the invention comprises: (1) dangling polysiloxane units derived from one or more monoethylenically functionalized polysiloxane-containing monomers and/or one or more monoethylenically-functionalized polysiloxane-containing macromers, wherein the dangling polysiloxane units are free of ethylenically unsaturated group; (2) hydrophilic units derived from one or more hydrophilic vinylic monomers; (3) crosslinking units derived from at least one polysiloxane-containing crosslinker and/or at least one silicone-free crosslinker; and (4) optionally hydrophobic units derived from at least one hydrophobic vinylic monomer, wherein the prepolymer comprises multiple ethylenically unsaturated groups and is capable of being actinically crosslinked, in the absence of one or more monomers, to form a silicone hydrogel material.
- the dangling polysiloxane-containing units of the prepolymer each should be free of any ethylenically unsaturated groups.
- a prepolymer of the invention is obtained from an intermediary copolymer with pendant or terminal functional group by ethylenically functionalizing the intermediary copolymer to include multiple ethylenically unsaturated groups, according to any covalently coupling method.
- a pair of matching reactive groups can form a covalent bond or linkage under known coupling reaction conditions, such as, oxidation-reduction conditions, dehydration condensation conditions, addition conditions, substitution (or displacement) conditions, Diels-Alder reaction conditions, cationic crosslinking conditions, and epoxy hardening conditions.
- coupling reaction conditions such as, oxidation-reduction conditions, dehydration condensation conditions, addition conditions, substitution (or displacement) conditions, Diels-Alder reaction conditions, cationic crosslinking conditions, and epoxy hardening conditions.
- an amino group reacts with aldehyde group to form a Schiff base which may further be reduced; an amino group reacts with an acid chloride to form an amide linkage (—CO—N—); an amino group reacts with an isocyanate to form a urea linkage; an hydroxyl reacts with an isocyanate to form a urethane linkage; an hydroxyl reacts with an epoxy to form an ether linkage (—O—); a hydroxyl reacts with an acid chloride to form an ester linkage.
- Exemplary covalent bonds or linkage, which are formed between pairs of crosslinkable groups include without limitation, ester, ether, acetal, ketal, vinyl ether, carbamate, urea, urethane, amine, amide, enamine, imine, oxime, amidine, iminoester, carbonate, orthoester, phosphonate, phosphinate, sulfonate, sulfinate, sulfide, sulfate, disulfide, sulfinamide, sulfonamide, thioester, aryl, silane, siloxane, heterocycles, thiocarbonate, thiocarbamate, and phosphonamide.
- Exemplary reactive groups include hydroxyl group, amine group, amide group, anhydride group, sulfhydryl group, —COOR (R and R′ are hydrogen or C 1 to C 8 alkyl groups), halide (chloride, bromide, iodide), acyl chloride, isothiocyanate, isocyanate, monochlorotriazine, dichlorotriazine, mono- or di-halogen substituted pyridine, mono- or di-halogen substituted diazine, phosphoramidite, maleimide, aziridine, sulfonyl halide, hydroxysuccinimide ester, hydroxysulfosuccinimide ester, imido ester, hydrazine, axidonitrophenyl group, azide, 3-(2-pyridyl dithio)proprionamide, glyoxal, aldehyde, epoxy.
- R and R′ are hydrogen or C 1 to C 8 al
- a carbodiimide can be used in the coupling of a carboxyl and an amine to form an amide linkage between the molecules being coupled.
- carbodiimides are 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), N,N′-dicyclohexylcarbodiimide (DCC), 1-cylcohexyl-3-(2-morpholinoethyl)carbodiimide, diisopropyl carbodiimide, or mixtures thereof.
- N-hydroxysuccinimide (NHS) or N-hydroxysulfosuccinimide may be desirably included in carbodiimide (e.g., EDC)-mediated coupling reaction to improve coupling (conjugation) efficiency.
- EDC couples NHS to carboxyls, resulting in an NHS-activated site on a molecule.
- the formed NHS-ester can react with amines to form amides.
- the intermediary copolymer with pendant or terminal functional groups is obtained by copolymerization of a polymerizable composition comprising (1) at least one monoethylenically functionalized polysiloxane-containing monomer and/or at least one monoethylenically unsaturated polysiloxane-containing macromer, (2) at least one hydrophilic vinylic monomer (i.e., having one ethylenically unsaturated group), (3) at least one polysiloxane-containing crosslinker and/or at least one silicone-free crosslinker, and (4) optionally at least one hydrophobic vinylic monomer, provided that at least one of components (2)-(4) further comprises at least one functional group through which an ethylenically unsaturated group can be covalently linked to the obtained intermediary copolymer.
- a polymerizable composition comprising (1) at least one monoethylenically functionalized polysiloxane-containing monomer and/or at least one monoethylenically unsaturated poly
- the intermediary copolymer with pendant or terminal functional groups is obtained by copolymerization of a composition comprising (1) at least one monoethylenically functionalized polysiloxane-containing monomer and/or at least one monoethylenically unsaturated polysiloxane-containing macromer, (2) at least one hydrophilic vinylic monomer (i.e., having one ethylenically unsaturated group), (3) at least one polysiloxane-containing crosslinker and/or at least one silicone-free crosslinker, (4) optionally at least one hydrophobic vinylic monomer, and (5) at least one chain transfer agent having a functional group through which an ethylenically unsaturated group can be covalently linked to the obtained intermediary copolymer.
- a composition comprising (1) at least one monoethylenically functionalized polysiloxane-containing monomer and/or at least one monoethylenically unsaturated polysiloxane-containing macromer, (2) at
- Any known suitable monoethylenically functionalized polysiloxane-containing monomers or macromers i.e., polysiloxane-containing monomers or macromers with one sole ethylenically unsaturated group
- suitable monoethylenically functionalized polysiloxane-containing monomers or macromers i.e., polysiloxane-containing monomers or macromers with one sole ethylenically unsaturated group
- a preferred class of monoethylenically functionalized polysiloxane-containing monomers or macromers are those defined by formula (I)
- R 14 denotes —COO—, —CONR 14 —, —OCOO—, or —OCONR 14 —, where each R 14 is independently H or C 1 -C 7 alkyl;
- R 11 denotes a divalent C 1 -C 25 alkyl or C 6 -C 30 aryl radical, which may interrupted by —O—, —COO—, —CONR 14 —, —OCOO— or —OCONR 14 — and may comprise hydroxy group, primary, secondary, or tertiary amine group, carboxy group, or carboxylic acid;
- R 12 is a monovalent C 1 -C 25 alkyl or C 6 -C 30 aryl radical, which may interrupted by —O—, —COO—, —CONR 14 —, —OCOO— or —OCONR 14 — and may comprise hydroxy group, primary, secondary, or tertiary amine group, or carboxylic acid;
- Preferred examples of such monomers or macromers are monomethacrylated or monoacrylated polydimethylsiloxanes of various molecular weight (e.g., mono-3-methacryloxypropyl terminated, mono-butyl terminated polydimethylsiloxane or mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydimethylsiloxane).
- monoethylenically functionalized polysiloxanes can be obtained by ethylenically functionalizing of a monofunctionalized polysiloxanes (i.e., with one sole terminal functional group, such as, e.g., —NH 2 , —OH, —COOH, epoxy group, etc.) as described above.
- a monofunctionalized polysiloxanes i.e., with one sole terminal functional group, such as, e.g., —NH 2 , —OH, —COOH, epoxy group, etc.
- Suitable monofunctionalized polysiloxanes are commercially available, e.g., from Aldrich, ABCR GmbH & Co., Fluorochem, or Gelest, Inc, Morrisville, Pa.
- hydrophilic vinylic monomer can be used in the actinically polymerizable composition for preparing the intermediary copolymer with pendant or terminal functional groups.
- Suitable hydrophilic vinylic monomers are, without this being an exhaustive list, hydroxyl-substituted hydroxyl-substituted C 1 -C 8 alkylacrylates and methacrylates, acrylamide, methacrylamide, C 1 -C 8 alkylacrylamides, C 1 -C 8 alkylmethacrylamides, ethoxylated acrylates, ethoxylated methacrylates, hydroxyl-substituted C 1 -C 8 alkylacrylamides, hydroxyl-substituted C 1 -C 8 alkylmethacrylamides, hydroxyl-substituted lower alkyl vinyl ethers, sodium vinylsulfonate, sodium styrenesulfonate, 2-acrylamido-2-methylpropanesulfonic acid, N-viny
- hydrophilic vinylic monomers are N,N-dimethylacrylamide (DMA), 2-hydroxyethylmethacrylate (HEMA), 2-hydroxyethyl acrylate (HEA), hydroxypropyl acrylate, hydroxypropyl methacrylate (HPMA), trimethylammonium 2-hydroxy propylmethacrylate hydrochloride, aminopropyl methacrylate hydrochloride, dimethylaminoethyl methacrylate (DMAEMA), glycerol methacrylate (GMA), N-vinyl-2-pyrrolidone (NVP), dimethylaminoethylmethacrylamide, acrylamide, methacrylamide, allyl alcohol, vinylpyridine, N-(1,1dimethyl-3-oxobutyl)acrylamide, acrylic acid, a C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of from 200 to 1500, methacrylic acid, N-vin
- polysiloxane-containing crosslinkers refers to polysiloxane-containing compounds, macromers or prepolymer, which comprises two or more ethylenically unsaturated groups.
- polysiloxane-containing crosslinkers include without limitation dimethacrylated or diacrylated polydimethylsiloxanes of various molecular weight; vinyl terminated polydimethylsiloxanes of various molecular weight; methacrylamide-terminated polydimethylsiloxanes; acrylamide-terminated polydimethylsiloxanes; acrylate-terminated polydimethylsiloxanes; methacrylate-terminated polydimethylsiloxanes; bis-3-methacryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane; N,N,N′,N′-tetrakis(3-methacryloxy-2-hydroxypropyl)-alpha,omega-bis-3-aminopropyl
- di and triblock macromers consisting of polydimethylsiloxane and polyalkyleneoxides (e.g., methacrylate end capped polyethyleneoxide-block-polydimethylsiloxane-block-polyethyleneoxide); and mixtures thereof.
- perfluoroalkyl ether crosslinkers such as those disclosed in U.S. Pat. No. 7,091,283 (herein incorporated by reference in its entirety), can also be used as crosslinkers in the invention.
- di- or multi-ethylenically functionalized polysiloxanes can be obtained by ethylenically functionalizing of a di- or multi-functionalized polysiloxanes (i.e., with two or more terminal functional groups, such as, e.g., —NH 2 , —OH, —COOH, epoxy groups, etc.) as described above.
- Suitable di- or multi-functionalized polysiloxanes are commercially available, e.g., from Aldrich, ABCR GmbH & Co., Fluorochem, or Gelest, Inc, Morrisville, Pa.
- silicone-free crosslinkers are vinylic compounds, macromers, or prepolymers, having two or more ethylenically unsaturated groups.
- silicone-free crosslinkers include without limitation tetraethyleneglycol dimethacrylate (TEGDMA), triethyleneglycol dimethacrylate (TrEGDMA), ethyleneglycol dimethacylate (EGDMA), ethylenediamine dimethyacrylamide, glycerol dimethacrylate and combinations thereof.
- TEGDMA tetraethyleneglycol dimethacrylate
- TrEGDMA triethyleneglycol dimethacrylate
- EGDMA ethyleneglycol dimethacylate
- ethylenediamine dimethyacrylamide ethylenediamine dimethyacrylamide
- glycerol dimethacrylate ethylenediamine dimethyacrylamide
- hydrophilic prepolymers with multiple acryloyl or methacryloyl groups include, but are not limited to, a water-soluble crosslinkable poly(vinyl alcohol) prepolymer described in U.S. Pat. Nos. 5,583,163 and 6,303,687; a water-soluble vinyl group-terminated polyurethane prepolymer described in U.S. Patent Application Publication No. 2004/0082680; derivatives of a polyvinyl alcohol, polyethyleneimine or polyvinylamine, which are disclosed in U.S. Pat. No. 5,849,841; a water-soluble crosslinkable polyurea prepolymer described in U.S. Pat. No.
- crosslinkable polyacrylamide crosslinkable statistical copolymers of vinyl lactam, MMA and a comonomer, which are disclosed in EP 655,470 and U.S. Pat. No. 5,712,356
- crosslinkable copolymers of vinyl lactam, vinyl acetate and vinyl alcohol which are disclosed in EP 712,867 and U.S. Pat. No. 5,665,840
- polyether-polyester copolymers with crosslinkable side chains which are disclosed in EP 932,635 and U.S. Pat. No.
- hydrophobic vinylic monomers can be used in the actinically polymerizable composition for preparing the intermediary copolymer with pendant or terminal functional groups.
- Suitable hydrophobic vinylic monomers include, without limitation, silicone-containing vinylic monomers, C 1 -C 18 -alkylacrylates and -methacrylates, C 3 -C 18 alkylacrylamides and -methacrylamides, acrylonitrile, methacrylonitrile, vinyl-C 1 -C 18 -alkanoates, C 2 -C 18 -alkenes, C 2 -C 18 -halo-alkenes, styrene, C 1 -C 6 -alkylstyrene, vinylalkylethers in which the alkyl moiety has 1 to 6 carbon atoms, C 2 -C 10 -perfluoralkyl-acrylates and -methacrylates or correspondingly partially fluorinated acrylates and methacrylates, C 3 -C 12
- hydrophobic vinylic monomers examples include methylacrylate, ethyl-acrylate, propylacrylate, isopropylacrylate, cyclohexylacrylate, 2-ethylhexylacrylate, methylmethacrylate, ethylmethacrylate, propyl methacrylate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, styrene, chloroprene, vinyl chloride, vinylidene chloride, acrylonitrile, 1-butene, butadiene, methacrylonitrile, vinyl toluene, vinyl ethyl ether, perfluorohexylethyl-thio-carbonyl-aminoethyl-methacrylate, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoro-isopropyl methacrylate, and hexafluorobutyl meth
- the chain transfer agent may comprise one or more thiol groups, for example two or most preferably one thiol group.
- Suitable chain transfer agents include without limitation 2-mercaptoethanol, 2-aminoethanethiol, 2-mercaptopropinic acid, thioglycolic acid, thiolactic acid, or other hydroxymercaptanes, aminomercaptans, carboxyl-containing mercaptanes, and mixtures thereof.
- a chain transfer agent comprises a functional group in addition to one or more thiol groups, it can be incorporated into the resultant intermediary copolymer and provide functionality for subsequent addition of an ethylenically unsaturated group to the intermediary copolymer.
- a chain transfer agent can also be used to control the molecular weight of the resultant copolymer.
- Any know suitable vinylic monomer containing at least one functional group can be used in the actinically polymerizable composition for preparing the intermediary copolymer with pendant or terminal functional groups.
- the functional groups of units derived from such vinylic monomer can be used in ethylenically functionalizing the intermediary copolymers.
- Preferred examples of such vinylic monomers includes methacrylic acid (MAA), acrylic acid, glycidylmethacrylate, glycidylacrylate, HEMA, HEA, aminopropyl methacrylate hydrochloride, methacrylic anhydride, N-hydroxymethylacrylamide (NHMA), 2-bromoethylmethacrylate, and vinylbenzylchloride.
- a vinylic monomer can be used both as a hydrophilic vinylic monomer and as a functionalizing vinylic monomer in the actinically polymerizable composition for preparing the intermediary copolymer with pendant or terminal functional groups.
- the hydrophilic vinylic monomer is devoid of functional groups (e.g., DMA, NVP).
- a polymerizable composition for making an intermediary copolymer of the invention further comprises at least one silicone-containing vinylic monomer.
- silicone-containing vinylic monomers examples include, without limitation, 3-methacryloxy propylpentamethyldisiloxane, bis(methacryloxypropyl)tetramethyl-disiloxane, N-[tris(trimethylsiloxy)silylpropyl]acrylamide, N-[tris(trimethylsiloxy)silylpropyl]methacrylamide, and tristrimethylsilyloxysilylpropyl methacrylate (TRIS), N-[tris(trimethylsiloxy)silylpropyl]methacrylamide (“TSMAA”), N-[tris(trimethylsiloxy)-silylpropyl]acrylamide (“TSAA”), (3-methacryloxy-2-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane), (3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethyls)propyltris(trimethyls)
- the polymerizable composition for preparing an intermediary copolymer can be a melt, a solventless liquid in which all necessary components are blended together preferably in the presence of one or more blending vinylic monomers, or a solution in which all necessary component is dissolved in a solvent, such as water, an organic solvent, or mixture thereof, as known to a person skilled in the art.
- Example of organic solvents includes without limitation tetrahydrofuran, tripropylene glycol methyl ether, dipropylene glycol methyl ether, ethylene glycol n-butyl ether, diethylene glycol n-butyl ether, diethylene glycol methyl ether, ethylene glycol phenyl ether, propylene glycol methyl ether, propylene glycol methyl ether acetate, dipropylene glycol methyl ether acetate, propylene glycol n-propyl ether, dipropylene glycol n-propyl ether, tripropylene glycol n-butyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, tripropylene glycol n-butyl ether, propylene glycol phenyl ether dipropylene glycol dimethyl ether, polyethylene glycols, polypropylene glycols, ethyl acetate
- the one or more blending vinylic monomers are in an amount sufficient to dissolve both hydrophilic and hydrophobic components of the actinically polymerizable composition.
- a “blending vinylic monomer” refers to a vinylic monomer which can function both as a solvent to dissolve both hydrophilic and hydrophobic components of an actinically polymerizable composition and as one of polymerizable components to be polymerized to form a silicone hydrogel material.
- the blending vinylic monomer is present in the actinically polymerizable composition in an amount of from about 5% to about 30% by weight.
- Any suitable vinylic monomers capable of dissolving both hydrophilic and hydrophobic components of a polymerizable composition of the invention to form a solution, can be used in the invention.
- Preferred examples of blending vinylic monomers include, without limitation, aromatic vinylic monomers, cycloalkyl-containing vinylic monomers. Those preferred blending monomers can increase the predominant glass transition temperature of a silicone hydrogel material prepared by curing a polymerizable composition containing those preferred blending monomer.
- aromatic vinylic monomers examples include styrene, 2,4,6-trimethylstyrene (TMS), t-butyl styrene (TBS), 2,3,4,5,6-pentafluorostyrene, benzyl methacrylate, divinylbenzene, and 2-vinylnaphthalene. Of these monomers, a styrene-containing monomer is preferred.
- a styrene-containing monomer is defined herein to be a monomer that contains a vinyl group bonded directly to a phenyl group in which the phenyl group can be substituted by other than a fused ring, e.g., as above with one to three C 1 -C 6 alkyl groups.
- Styrene itself [H 2 C ⁇ CH—C 6 H 5 ] is a particularly preferred styrene-containing monomer.
- a cycloalkyl-containing vinylic monomer is defined herein to be a vinylic monomer containing a cycloalkyl which can be substituted by up to three C 1 -C 6 alkyl groups.
- Preferred cycloalkyl-containing vinylic monomers include, without limitation, acrylates and methacrylates each comprising a cyclopentyl or cyclohexyl or cycloheptyl, which can be substituted by up to 3 C 1 -C 6 alkyl groups.
- Examples of preferred cycloalkyl-containing vinylic monomers include isobornylmethacrylate, isobornylacrylate, cyclohexylmethacrylate, cyclohexylacrylate, and the like.
- the stoichiometry of the hydrophilic monomer, crosslinker and chain transfer agent in the polymerizable composition for preparing an intermediary copolymer may be chosen within wide limits and is strongly dependant on the intended use.
- a molar ratio of from 0.5 to 5 equivalents chain transfer agent: 1-3 equivalents monoethylenically functionalized polysiloxane-containing monomer and macromer (in total):1 equivalent crosslinker (including polysiloxane-containing crosslinker and silicone-free crosslinker): 5 to 60 equivalents hydrophilic monomer(s) has proven as practicable for biomedical purposes.
- a preferred range is from 1 to 3 molar equivalents chain transfer agent: 1-3 equivalents monoethylenically functionalized polysiloxane-containing monomer and macromer (in total): 1 equivalent crosslinker (including polysiloxane-containing crosslinker and silicone-free crosslinker): 10 to 50 molar equivalents hydrophilic monomer(s).
- the weight average molecular weight of the resulting copolymers is strongly dependent, for example, on the amount of chain transfer agent used, preferably from 3000 to 1000000, preferably from 5000 to 500000, more preferably from 7000 to 250000 daltons.
- the copolymerization of a polymerizable composition for preparing an intermediary copolymer may be induced photochemically or preferably thermally.
- Suitable thermal polymerization initiators are known to the skilled artisan and comprise, for example peroxides, hydroperoxides, azo-bis(alkyl- or cycloalkylnitriles), persulfates, percarbonates or mixtures thereof.
- Examples are benzoylperoxide, tert.-butyl peroxide, di-tert.-butyl-diperoxyphthalate, tert.-butyl hydroperoxide, azo-bis(isobutyronitrile) (AIBN), 1,1-azodiisobutyramidine, 1,1′-azo-bis (1-cyclohexanecarbonitrile), 2,2′-azo-bis(2,4-dimethylvaleronitrile) and the like.
- the polymerization is carried out conveniently in an above-mentioned solvent at elevated temperature, for example at a temperature of from 25 to 100° C. and preferably 40 to 80° C.
- the reaction time may vary within wide limits, but is conveniently, for example, from 1 to 24 hours or preferably from 2 to 12 hours. It is advantageous to previously degas the components and solvents used in the polymerization reaction and to carry out said copolymerization reaction under an inert atmosphere, for example under a nitrogen or argon atmosphere. Copolymerization can yield optically clear well-defined copolymers which may be worked up in conventional manner using for example extraction, precipitation, ultrafiltration and the like techniques.
- the dangling polysiloxane units is present in the prepolymer in an amount sufficient to provide the lens made from the prepolymer with a reduction in modulus of at least about 10% or more, preferably at least about 20% or more, even more preferably at least about 30% or more, most preferably at least about 40% or more.
- the dangling polysiloxane units is present in the prepolymer in an amount sufficient to provide the lens made from the prepolymer with an increase in ion permeability of at least about 20% or more, preferably at least about 40% or more, even more preferably at least about 60% or more.
- the amount of the dangling polysiloxane units in the prepolymer can be changed by adjusting the amount of the one or more monoethylenically functionalized polysiloxane-containing monomers and/or one or more monoethylenically-functionalized polysiloxane-containing macromers in the polymerizable composition for preparing the intermediary copolymer with pendant or terminal functional groups while maintaining the total weight percentage of all polysiloxane-containing polymerizable components.
- a prepolymer of the invention comprises: (1) from about 2% to about 70% by weight, preferably from about 5% to about 40%, of dangling polysiloxane units derived from one or more monoethylenically functionalized polysiloxane-containing monomers and/or macromers; (2) from about 10% to about 70%, preferably from about 20% to 60% by weight, by weight of hydrophilic units derived from one or more hydrophilic monomers; (3) from 0 to about 70%, preferably from about 1% to about 60%, more preferably from about 5% to about 50% by weight of crosslinking polysiloxane units derived from a polysiloxane-containing crosslinker; (4) from 0 to about 5%, more preferably from 0 to about 2% by weight of silicone-free crosslinker; and (5) from about 0 to about 35%, preferably from about 1% to about 30% by weight of silicone-containing units derived from one or more silicone-containing vinylic monomers.
- ethylenical functionalization of the intermediary copolymer can be carried out by covalently attaching ethylenically unsaturated groups to the functional groups (e.g., amine, hydroxyl, carboxyl, isocyanate, epoxy groups) of the intermediary copolymer.
- the functional groups e.g., amine, hydroxyl, carboxyl, isocyanate, epoxy groups
- a coupling agent such as, e.g., EDC, diisocyanate, or diacid chloride
- vinylic monomers include, without limitation, for reacting with terminal hydroxy groups, 2-isocyanatoethyl methacrylate, methacrylic anhydride, 3-isopropenyl-alpha, alpha-dimethylbenzyl isocyanate, acryloyl chloride, or methacryloyl chloride, glycidyl methacrylate; for reacting with terminal amine groups, 2-isocyanatoethyl methacrylate, 3-isopropenyl-alpha, alpha-dimethylbenzyl isocyanate, methacrylic anhydride, acrylic acid, methacrylic acid, acryloyl chloride, or methacryloyl chloride; for reacting with terminal carboxy groups in the presence of EDC, vinylamine, 2-aminoethyl methacrylate or 3-aminopropyl methacrylamide.
- a prepolymer of the invention is capable of forming, preferably in the absence of any hydrophilic vinylic monomer, a silicone hydrogel or contact lens, which has a high oxygen permeability (characterized by an apparent oxygen permeability of at least 40 barrers, preferably at least about 60 barrers, even more preferably at least 80 barrers) and an elastic modulus of preferably about 1.5 MPa or less, more preferably about 1.2 or less, even more preferably from about 0.4 MPa to about 1.0 MPa.
- a high oxygen permeability characterized by an apparent oxygen permeability of at least 40 barrers, preferably at least about 60 barrers, even more preferably at least 80 barrers
- an elastic modulus preferably about 1.5 MPa or less, more preferably about 1.2 or less, even more preferably from about 0.4 MPa to about 1.0 MPa.
- a prepolymer of the invention can be used to prepare silicone hydrogel contact lenses having a relatively low elastic modulus while having a relatively high oxygen permeability.
- the prepolymers used in the invention are previously purified in a manner known per se, for example by precipitation with organic solvents, such as acetone, filtration and washing, extraction in a suitable solvent, dialysis or ultrafiltration, ultrafiltration being especially preferred.
- organic solvents such as acetone, filtration and washing
- the prepolymers can be obtained in a pure form, for example in the form of concentrated solutions that are free, or at least substantially free, from reaction products, such as salts, and from starting materials, such as, for example, non-polymeric constituents.
- the preferred purification process for the prepolymers used in the process according to the invention, ultrafiltration can be carried out in a manner known per se. It is possible for the ultrafiltration to be carried out repeatedly, for example from two to ten times.
- the ultrafiltration can be carried out continuously until the selected degree of purity is attained.
- the selected degree of purity can, in principle, be as high as desired.
- a suitable measure for the degree of purity is, for example, the concentration of dissolved salts obtained as by-products, which can be determined simply in a known manner.
- the device will not require subsequent purification such as, for example, costly and complicated extraction of unpolymerized matrix-forming material.
- crosslinking of the prepolymer can take place absent a solvent or in aqueous solution so that a subsequent solvent exchange or the hydration step is not necessary.
- the invention provides a soft contact lens.
- the soft contact lens of the invention comprises: a silicone hydrogel material that is obtained by curing a lens-forming material in a mold, wherein the lens-forming material comprises an actinically crosslinkable prepolymer and is substantially free of vinylic monomers and crosslinking agent with molecular weight of less than 1500 dalton, wherein the prepolymer comprises (1) dangling polysiloxane units derived from one or more monoethylenically functionalized polysiloxane-containing monomers and/or one or more monoethylenically-functionalized polysiloxane-containing macromers, wherein the dangling polysiloxane units is free of ethylenically unsaturated groups; (2) hydrophilic units derived from one or more hydrophilic vinylic monomers; (3) crosslinking units derived from at least one polysiloxane-containing crosslinker and/or at least one silicone-free crosslinker; (4) multiple ethylenically
- a lens-forming material is a composition, which can be a solution or a melt at a temperature from about 20° C. to about 85° C.
- a lens-forming material is a solution of at least one prepolymer of the invention and other desirable components in water, or an organic solvent, or a mixture of water and one or more organic solvents.
- a solution of at least one prepolymer can be prepared by dissolving the prepolymer and other components in any suitable solvent known to a person skilled in the art. Examples of suitable solvents are described above.
- the lens-forming material can optionally but preferably does not comprise one or more vinylic monomer and/or one or more crosslinking agents (i.e., compounds with two or more ethylenically unsaturated groups and with molecular weight less than 700 Daltons).
- crosslinking agents i.e., compounds with two or more ethylenically unsaturated groups and with molecular weight less than 700 Daltons.
- the amount of those components should be low such that the final ophthalmic device does not contain unacceptable levels of unpolymerized monomers and/or crosslinking agents.
- the presence of unacceptable levels of unpolymerized monomers and/or crosslinking agents will require extraction to remove them, which requires additional steps that are costly and inefficient.
- the lens-forming material is substantially free of vinylic monomer and crosslinking agent (i.e., preferably about 2% or less, more preferably about 1% or less, even more preferably about 0.5% or less by weight of combination of vinylic monomer and crosslinking agent).
- a lens-forming material can also comprise various components, such as, for example, polymerization initiators (e.g., photoinitiator or thermal initiator), a visibility tinting agent (e.g., dyes, pigments, or mixtures thereof), UV-blocking (absorbing) agent, photosensitizers, inhibitors, antimicrobial agents (e.g., preferably silver nanoparticles or stabilized silver nanoparticles), bioactive agent, leachable lubricants, fillers, and the like, as known to a person skilled in the art.
- polymerization initiators e.g., photoinitiator or thermal initiator
- a visibility tinting agent e.g., dyes, pigments, or mixtures thereof
- UV-blocking (absorbing) agent e.g., photosensitizers, inhibitors, antimicrobial agents (e.g., preferably silver nanoparticles or stabilized silver nanoparticles), bioactive agent, leachable lubricants, fillers, and the like
- Initiators for example, selected from materials well known for such use in the polymerization art, may be included in the lens-forming material in order to promote, and/or increase the rate of, the polymerization reaction.
- An initiator is a chemical agent capable of initiating polymerization reactions.
- the initiator can be a photoinitiator or a thermal initiator.
- a photoinitiator can initiate free radical polymerization and/or crosslinking by the use of light.
- Suitable photoinitiators are benzoin methyl ether, diethoxyacetophenone, a benzoylphosphine oxide, 1-hydroxycyclohexyl phenyl ketone and Darocur and Irgacur types, preferably Darocur 1173® and Darocur 2959®.
- benzoylphosphine initiators include 2,4,6-trimethylbenzoyldiphenylophosphine oxide; bis-(2,6-dichlorobenzoyl)-4-N-propylphenylphosphine oxide; and bis-(2,6-dichlorobenzoyl)-4-N-butylphenylphosphine oxide.
- Reactive photoinitiators which can be incorporated, for example, into a macromer or can be used as a special monomer are also suitable. Examples of reactive photoinitiators are those disclosed in EP 632 329, herein incorporated by reference in its entirety.
- the polymerization can then be triggered off by actinic radiation, for example light, in particular UV light of a suitable wavelength.
- the spectral requirements can be controlled accordingly, if appropriate, by addition of suitable photosensitizers
- thermal initiators examples include, but are not limited to, 2,2′-azobis(2,4-dimethylpentanenitrile), 2,2′-azobis(2-methylpropanenitrile), 2,2′-azobis(2-methylbutanenitrile), peroxides such as benzoyl peroxide, and the like.
- the thermal initiator is azobisisobutyronite (AIBN).
- pigments examples include any colorant permitted in medical devices and approved by the FDA, such as D&C Blue No. 6, D&C Green No. 6, D&C Violet No. 2, carbazole violet, certain copper complexes, certain chromium oxides, various iron oxides, phthalocyanine green, phthalocyanine blue, titanium dioxides, etc. See Marmiom DM Handbook of U.S. Colorants for a list of colorants that may be used with the present invention.
- a more preferred embodiment of a pigment include (C.I. is the color index no.), without limitation, for a blue color, phthalocyanine blue (pigment blue 15:3, C.I. 74160), cobalt blue (pigment blue 36, C.I.
- Toner cyan BG (Clariant), Permajet blue B2G (Clariant); for a green color, phthalocyanine green (Pigment green 7, C.I. 74260) and chromium sesquioxide; for yellow, red, brown and black colors, various iron oxides; PR122, PY154, for violet, carbazole violet; for black, Monolith black C-K (CIBA Specialty Chemicals).
- the bioactive agent incorporated in the polymeric matrix is any compound that can prevent a malady in the eye or reduce the symptoms of an eye malady.
- the bioactive agent can be a drug, an amino acid (e.g., taurine, glycine, etc.), a polypeptide, a protein, a nucleic acid, or any combination thereof.
- amino acid e.g., taurine, glycine, etc.
- drugs useful herein include, but are not limited to, rebamipide, ketotifen, olaptidine, cromoglycolate, cyclosporine, nedocromil, levocabastine, lodoxamide, ketotifen, or the pharmaceutically acceptable salt or ester thereof.
- bioactive agents include 2-pyrrolidone-5-carboxylic acid (PCA), alpha hydroxyl acids (e.g., glycolic, lactic, malic, tartaric, mandelic and citric acids and salts thereof, etc.), linoleic and gamma linoleic acids, and vitamins (e.g., B5, A, B6, etc.).
- PCA 2-pyrrolidone-5-carboxylic acid
- alpha hydroxyl acids e.g., glycolic, lactic, malic, tartaric, mandelic and citric acids and salts thereof, etc.
- linoleic and gamma linoleic acids e.g., B5, A, B6, etc.
- leachable lubricants include without limitation mucin-like materials and non-crosslinkable hydrophilic polymers (i.e., without ethylenically unsaturated groups).
- mucin-like materials include without limitation polyglycolic acid, polylactides, collagen, hyaluronic acid, and gelatin.
- any hydrophilic polymers or copolymers without any ethylenically unsaturated groups can be used as leachable lubricants.
- Preferred examples of non-crossllinkable hydrophilic polymers include, but are not limited to, polyvinyl alcohols (PVAs), polyamides, polyimides, polylactone, a homopolymer of a vinyl lactam, a copolymer of at least one vinyl lactam in the presence or in the absence of one or more vinylic comonomers, a homopolymer of acrylamide or methacrylamide, a copolymer of acrylamide or methacrylamide with one or more hydrophilic vinylic monomers, polyethylene oxide (i.e., polyethylene glycol (PEG)), a polyoxyethylene derivative, poly-N—N-dimethylacrylamide, polyacrylic acid, poly 2 ethyl oxazoline, heparin polysaccharides, polysaccharides, and mixtures thereof.
- the molecular weight of the non-crosslinkable hydrophilic polymer is preferably from about 20,000 to about 1,500,000 daltons, more preferably from about 50,000 to 1,200,000 daltons, even more preferably from 100,000 to 1,000,000 daltons.
- the lens-forming material can be introduced (dispensed) into a cavity formed by a mold according to any known methods.
- a mold for cast molding
- a mold generally comprises at least two mold sections (or portions) or mold halves, i.e. first and second mold halves.
- the first mold half defines a first molding (or optical) surface and the second mold half defines a second molding (or optical) surface.
- the first and second mold halves are configured to receive each other such that a lens forming cavity is formed between the first molding surface and the second molding surface.
- the molding surface of a mold half is the cavity-forming surface of the mold and in direct contact with lens-forming material.
- Methods of manufacturing mold sections for cast-molding a contact lens are generally well known to those of ordinary skill in the art.
- the process of the present invention is not limited to any particular method of forming a mold. In fact, any method of forming a mold can be used in the present invention.
- the first and second mold halves can be formed through various techniques, such as injection molding or lathing. Examples of suitable processes for forming the mold halves are disclosed in U.S. Pat. No. 4,444,711 to Schad; U.S. Pat. No. 4,460,534 to Boehm et al.; U.S. Pat. No. 5,843,346 to Morrill; and U.S. Pat. No. 5,894,002 to Boneberger et al., which are also incorporated herein by reference.
- Virtually all materials known in the art for making molds can be used to make molds for preparing ocular lenses.
- polymeric materials such as polyethylene, polypropylene, polystyrene, PMMA, cyclic olefin copolymers (e.g., Topas® COC from Ticona GmbH of Frankfurt, Germany and Summit, N.J.; Zeonex® and Zeonor® from Zeon Chemicals LP, Louisville, Ky.), or the like can be used.
- Other materials that allow UV light transmission could be used, such as quartz, glass, CaF 2 , and sapphire.
- reusable molds can be used.
- reusable molds made of quartz or glass are those disclosed in U.S. Pat. No. 6,627,124, which is incorporated by reference in their entireties.
- the lens-forming material is poured into a mold consisting of two mold halves, the two mold halves not touching each other but having a thin gap of annular design arranged between them. The gap is connected to the mold cavity, so that excess lens-forming material can flow into the gap.
- Reusable molds can also be made of a cyclic olefin copolymer, such as for example, Topas® COC grade 8007-S10 (clear amorphous copolymer of ethylene and norbornene) from Ticona GmbH of Frankfurt, Germany and Summit, N.J., Zeonex® and Zeonor® from Zeon Chemicals LP, Louisville, Ky.
- a cyclic olefin copolymer such as for example, Topas® COC grade 8007-S10 (clear amorphous copolymer of ethylene and norbornene) from Ticona GmbH of Frankfurt, Germany and Summit, N.J., Zeonex® and Zeonor® from Zeon Chemicals LP, Louisville, Ky.
- the lens-forming material After the lens-forming material is dispensed into the mold, it is polymerized to produce a contact lens.
- Crosslinking and/or polymerizing may be initiated in the mold e.g. by means of actinic radiation, such as UV irradiation, ionizing radiation (e.g., gamma or X-ray irradiation).
- actinic radiation such as UV irradiation, ionizing radiation (e.g., gamma or X-ray irradiation).
- the mold containing the lens-forming material can be exposed to a spatial limitation of actinic radiation to crosslink the prepolymers.
- the crosslinking according to the invention may be effected in a very short time, e.g. in 60 minutes, advantageously in ⁇ 20 minutes, preferably in ⁇ 10 minutes, most preferably in ⁇ 5 minutes, particularly preferably in 1 to 60 seconds and most particularly in 1 to 30 seconds.
- the contact lenses according to the invention can be produced from one or more radiation-curable prepolymers of the invention in a very simple and efficient way compared with the prior art. This is based on many factors. On the one hand, the starting materials may be acquired or produced inexpensively. Secondly, there is the advantage that the prepolymers are surprisingly stable, so that they may undergo a high degree of purification. There is no practical need for subsequent purification, such as in particular complicated extraction of unpolymerized constituents after curing lenses. Furthermore, the new polymerization method can be used to produce contact lenses with desirable mechanical and physical properties. Finally, photo-polymerization is effected within a short period, so that from this point of view also the production process for the contact lenses according to the invention may be set up in an extremely economic way.
- Opening of the mold so that the molded article can be removed from the mold may take place in a manner known per se.
- the contact lens can be directly transformed in the usual way, by hydration, into a ready-to-use contact lens.
- Appropriate embodiments of hydration are known to the person skilled in the art, whereby ready-to-use contact lenses with very varied water content may be obtained.
- the contact lens is expanded, for example, in water, in an aqueous salt solution, especially an aqueous salt solution having an osmolarity of about 200 to 450 milli-Osmole in 1000 ml (unit: mOsm/ml), preferably about 250 to 350 mOsm/l and especially about 300 mOsm/l, or in a mixture of water or an aqueous salt solution with a physiologically compatible polar organic solvent, e.g. glycerol.
- Preference is given to expansions of the article in water or in aqueous salt solutions.
- the molded contact lens is produced from an aqueous solution of an already purified prepolymer according to the invention, then the crosslinked product also does not contain any troublesome impurities. It is therefore not necessary to carry out subsequent extraction. Since crosslinking is carried out in an essentially aqueous solution, it is additionally unnecessary to carry out subsequent hydration.
- the contact lenses obtained by this process are therefore notable, according to an advantageous embodiment, for the fact that they are suitable for their intended usage without extraction. By intended usage is understood, in this context, that the contact lenses can be used in the human eye.
- the molded contact lens is produced from a solvent solution of an already purified prepolymer according to the invention, it is not necessary to carry out subsequent extraction, but instead of hydration process to replace the solvent.
- the molded contact lenses can be further subjected to further processes, such as, for example, surface treatment, sterilization, and the like.
- a contact lens of the invention has an oxygen permeability of preferably at least about 40 barrers, more preferably at least about 60 barrers, even more preferably at least about 80 barrers; and an elastic modulus of about 1.5 MPa or less, preferably about 1.2 MPa or less, more preferably about 1.0 MPa or less.
- an oxygen permeability is an apparent (directly measured when testing a sample with a thickness of about 100 microns) oxygen permeability according to procedures described in Examples.
- a contact lens of the invention further has an ion permeability characterized by having an Ionoflux Diffusion Coefficient, D, of, preferably at least about 1.5 ⁇ 10 ⁇ 6 mm 2 /min, more preferably at least about 2.6 ⁇ 10 ⁇ 6 mm 2 /min, even more preferably at least about 6.4 ⁇ 10 ⁇ 6 mm 2 /min.
- D Ionoflux Diffusion Coefficient
- a contact lens of the invention further has a water content of preferably from about 15% to about 55%, more preferably from about 20% to about 38% by weight when fully hydrated.
- the water content of a silicone hydrogel contact lens can be measured according to Bulk Technique as disclosed in U.S. Pat. No. 5,849,811.
- the invention provides a method for producing soft contact lenses.
- the method comprises the steps of: comprising the steps of: providing a mold for making a soft contact lens, wherein the mold has a first mold half with a first molding surface defining the anterior surface of a contact lens and a second mold half with a second molding surface defining the posterior surface of the contact lens, wherein said first and second mold halves are configured to receive each other such that a cavity is formed between said first and second molding surfaces; introduce a lens-forming material into the cavity, wherein the lens-forming material comprises one or more actinically crosslinkable prepolymers and is substantially free of vinylic monomer and/or crosslinking agent, wherein each of said one or more prepolymers comprises (1) dangling polysiloxane units derived from one or more monoethylenically functionalized polysiloxane-containing monomers and/or one or more monoethylenically-functionalized polysiloxane-containing macromers, wherein the dangling polysilox
- Oxygen permeability measurements The oxygen permeability of a lens and oxygen transmissibility of a lens material is determined according to a technique similar to the one described in U.S. Pat. No. 5,760,100 and in an article by Winterton et al., (The Cornea: Transactions of the World Congress on the Cornea 111, H. D. Cavanagh Ed., Raven Press: New York 1988, pp 273-280), both of which are herein incorporated by reference in their entireties.
- Oxygen fluxes (J) are measured at 34° C. in a wet cell (i.e., gas streams are maintained at about 100% relative humidity) using a Dk1000 instrument (available from Applied Design and Development Co., Norcross, Ga.), or similar analytical instrument.
- An air stream having a known percentage of oxygen (e.g., 21%), is passed across one side of the lens at a rate of about 10 to 20 cm 3 /min., while a nitrogen stream is passed on the opposite side of the lens at a rate of about 10 to 20 cm 3 /min.
- a sample is equilibrated in a test media (i.e., saline or distilled water) at the prescribed test temperature for at least 30 minutes prior to measurement but not more than 45 minutes. Any test media used as the overlayer is equilibrated at the prescribed test temperature for at least 30 minutes prior to measurement but not more than 45 minutes.
- the stir motor's speed is set to 1200 ⁇ 50 rpm, corresponding to an indicated setting of 400 ⁇ 15 on the stepper motor controller.
- the barometric pressure surrounding the system, P measured is measured.
- the thickness (t) of the lens in the area being exposed for testing is determined by measuring about 10 locations with a Mitotoya micrometer VL-50, or similar instrument, and averaging the measurements.
- the oxygen concentration in the nitrogen stream i.e., oxygen which diffuses through the lens
- the oxygen transmissibility (Dk/t) of the material may be calculated by dividing the oxygen permeability (Dk app ) by the average thickness (t) of the lens.
- ion Permeability Measurements The ion permeability of a lens is measured according to procedures described in U.S. Pat. No. 5,760,100 (herein incorporated by reference in its entirety. The values of ion permeability reported in the following examples are relative ionoflux diffusion coefficients (D/D ref ) in reference to a lens material, Alsacon, as reference material. Alsacon has an ionoflux diffusion coefficient of 0.314 ⁇ 10 ⁇ 3 mm 2 /minute.
- Initiator solutions are prepared by dissolving a desired amount of an initiator in t-amyl alcohol as shown in Table 1. The resulting solution is stirred and degassed at room temperature 2 times for 5 minutes each below 50 mbar.
- a reactor solution temperature prepared above is rapidly raised to 68° C. At this temperature, an initiator solution is injected in while taking care to exclude oxygen from the system. This system is allowed to react for 5 hours when the temperature is rapidly reduced to room temperature.
- the cooled reaction solution is filtered through a Por 3 fritted Buchner funnel with 1-propanol rinsing.
- 0.016 g hydroxyl-TEMPO is added to the filtered solution.
- the solution is rotovapped at 45° C. and 80-100 mbar to remove the alcohols in three steps, each time replacing the removed alcohol with deionized water until less than ⁇ 5% solvent remained. This process results in an emulsion.
- a lens formulation is prepared from a prepolymer prepared above by mixing 65% prepolymer with 0.16% Irgacur 2959 (relative to total formulation) and 34.84% 1-propanol. After dissolution, the formulation is dosed into PP molds, cured under a Hamamatsu lamp at 4 mW/cm 2 for about 44 seconds (Example 2a) and about 60 seconds (Example 2b) respectively.
- the resulting lenses are demolded using water at room temperature. Lenses are not extracted. Lenses are autoclaved for 30 minutes at 121° C. in phosphate buffered saline. Lens properties are determined and reported in Table 3. It is found that by substituting about 3.45% of polysiloxane crosslinker with a monomethacrylate PDMS (for forming a prepolymer with dangling polysiloxane polymer chains), the resultant lenses have a reduction in modulus of about 44%
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Ophthalmology & Optometry (AREA)
- Mechanical Engineering (AREA)
- Eyeglasses (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
in which R1 and R2 are independently a monovalent C1-C10 alkyl, C1-C10 ether, C1-C10 fluoroalkyl, C1-C10 fluoroether, or C6-C18 aryl radical, which may comprise hydroxy group, primary, secondary, or tertiary amine group, carboxy group, or carboxylic acid; n is an integer of 4 or higher.
[(cm3 oxygen)/(cm2)(sec)(mm2 Hg)]×10−9
[(cm3 oxygen)(mm)/(cm2)(sec)(mm2 Hg)]×10−10
In accordance with the invention, a high oxygen permeability in reference to a material or a contact lens characterized by apparent oxygen permeability of at least 40 barrers or larger measured with a sample (film or lens) of 100 microns in thickness according to a coulometric method described in Examples.
D=−n′/(A×dc/dx)
where n′=rate of ion transport [mol/min]
ln(1−2C(t)/C(0))=−2APt/Vd
where: C(t)=concentration of sodium ions at time t in the receiving cell
in which E is the modulus of a testing lens obtained from a first prepolymer with dangling polysiloxane polymer chains and Econtrol is the modulus of a control lens obtained from a second prepolymer without dangling polysiloxane polymer chains but having substantially identical amount (by weight) of polysiloxane (based on the compositions for making both the first and second prepolymers) as shown in Example 2.
in which IP is the ion permeability of a testing lens obtained from a first prepolymer with dangling polysiloxane polymer chains and IPcontrol is the ion permeability of a control lens obtained from a second prepolymer without dangling polysiloxane polymer chains but having substantially identical amount (by weight) of polysiloxane (based on the compositions for making both the first and second prepolymers) as shown in Example 2.
in which X denotes —COO—, —CONR14—, —OCOO—, or —OCONR14—, where each R14 is independently H or C1-C7 alkyl; R11 denotes a divalent C1-C25 alkyl or C6-C30 aryl radical, which may interrupted by —O—, —COO—, —CONR14—, —OCOO— or —OCONR14— and may comprise hydroxy group, primary, secondary, or tertiary amine group, carboxy group, or carboxylic acid; R12 is a monovalent C1-C25 alkyl or C6-C30 aryl radical, which may interrupted by —O—, —COO—, —CONR14—, —OCOO— or —OCONR14— and may comprise hydroxy group, primary, secondary, or tertiary amine group, carboxy group, or carboxylic acid; R3, R4, R5′, R6, R7, R8, R9 and R10, independently of one another, are C1-C8-alkyl, C1-C4 alkyl- or C1-C4-alkoxy-substituted phenyl, fluoro(C1-C18-alkyl), cyano(C1-C12-alkyl), hydroxy-C1-C6-alkyl or amino-C1-C6-alkyl; x is the number 0 or 1, m and p independently of each other are an integer of from 5 to 700 and (m+p) is from 5 to 700. Preferred examples of such monomers or macromers are monomethacrylated or monoacrylated polydimethylsiloxanes of various molecular weight (e.g., mono-3-methacryloxypropyl terminated, mono-butyl terminated polydimethylsiloxane or mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydimethylsiloxane). Alternatively, monoethylenically functionalized polysiloxanes can be obtained by ethylenically functionalizing of a monofunctionalized polysiloxanes (i.e., with one sole terminal functional group, such as, e.g., —NH2, —OH, —COOH, epoxy group, etc.) as described above. Suitable monofunctionalized polysiloxanes are commercially available, e.g., from Aldrich, ABCR GmbH & Co., Fluorochem, or Gelest, Inc, Morrisville, Pa.
Dk app =Jt/(P oxygen)
where J=oxygen flux [microliters O2/cm2-minute]
TABLE 1 | |||
Reactant/Example | 2a (grams) | 2b (grams) | |
AIBN | 0.059 | 0.059 | |
t-amyl alcohol | 11.40 | 11.44 | |
Preparation of Reactor Solution
TABLE 2 | |
Example |
Reactant | 2a (grams) | 2b (grams) |
PDMS-11500 diacrylamide | 11.50 | 8.05 |
PDMS-5000 monomethacrylate “MCR-M17”* | NA | 3.45 |
Aminopropyl methacrylate hydrochloride | 1.33 | 1.33 |
Acrylic Acid | 0.04 | 0.04 |
Hydroxyethyl acrylate | 5.30 | 5.30 |
N,N-dimethylacrylamide | 7.96 | 7.96 |
t-amyl alcohol | 320.42 | 320.35 |
*from Gelest |
Preparation of Prepolymer
an increase in IP of about 109%
and substantially unchanged oxygen permeability (Dk).
TABLE 3 | |||||||
NVE, % | water | Dk* | Modulus | average | diameter | ||
Example | residual | content (%) | (barrer) | E′ (MPa) | ETB % | (mm) | IP# |
2a | 7.6 | 36 | 88 | 1.33 | 158 | 13.8 | 8.6 |
2b | 11.5 | 38 | 89 | 0.75 | 157 | 14.2 | 18 |
NVE: non-volatile extractable; | |||||||
*apparent Dk; ETB: elongation at break; | |||||||
#ion permeability relative to Alsacon. |
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/284,092 US8263679B2 (en) | 2007-03-22 | 2011-10-28 | Prepolymers with dangling polysiloxane-containing polymer chains |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US89632507P | 2007-03-22 | 2007-03-22 | |
US12/077,772 US8071658B2 (en) | 2007-03-22 | 2008-03-21 | Prepolymers with dangling polysiloxane-containing polymer chains |
US13/284,092 US8263679B2 (en) | 2007-03-22 | 2011-10-28 | Prepolymers with dangling polysiloxane-containing polymer chains |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/077,772 Division US8071658B2 (en) | 2007-03-22 | 2008-03-21 | Prepolymers with dangling polysiloxane-containing polymer chains |
Publications (2)
Publication Number | Publication Date |
---|---|
US20120046382A1 US20120046382A1 (en) | 2012-02-23 |
US8263679B2 true US8263679B2 (en) | 2012-09-11 |
Family
ID=39766782
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/077,772 Active 2029-03-27 US8071658B2 (en) | 2007-03-22 | 2008-03-21 | Prepolymers with dangling polysiloxane-containing polymer chains |
US13/284,092 Active US8263679B2 (en) | 2007-03-22 | 2011-10-28 | Prepolymers with dangling polysiloxane-containing polymer chains |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/077,772 Active 2029-03-27 US8071658B2 (en) | 2007-03-22 | 2008-03-21 | Prepolymers with dangling polysiloxane-containing polymer chains |
Country Status (12)
Country | Link |
---|---|
US (2) | US8071658B2 (en) |
EP (1) | EP2129513B1 (en) |
JP (1) | JP5484916B2 (en) |
KR (1) | KR101482808B1 (en) |
CN (1) | CN101641206B (en) |
AU (1) | AU2008228760B2 (en) |
BR (1) | BRPI0809271A2 (en) |
CA (1) | CA2679322C (en) |
MX (1) | MX2009010116A (en) |
RU (1) | RU2462361C2 (en) |
WO (1) | WO2008116131A2 (en) |
ZA (1) | ZA200904884B (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014093751A2 (en) | 2012-12-14 | 2014-06-19 | Novartis Ag | Amphiphilic siloxane-containing vinylic monomers and uses thereof |
WO2014093756A1 (en) | 2012-12-14 | 2014-06-19 | Novartis Ag | Actinically-crosslinkable amphiphilic prepolymers |
WO2014093764A1 (en) | 2012-12-14 | 2014-06-19 | Novartis Ag | Amphiphilic siloxane-containing (meth)acrylamides and uses thereof |
US9096025B2 (en) | 2008-07-21 | 2015-08-04 | Novartis Ag | Silicone hydrogel lenses with convertible comfort agents |
WO2015164630A1 (en) | 2014-04-25 | 2015-10-29 | Novartis Ag | Carbosiloxane vinylic monomers |
US9475827B2 (en) | 2012-12-14 | 2016-10-25 | Shin-Etsu Chemical Company, Ltd. | Tris(trimethyl siloxyl)silane vinylic monomers and uses thereof |
US9684095B2 (en) | 2014-04-25 | 2017-06-20 | Novartis Ag | Hydrophilized carbosiloxane vinylic monomers |
US10053597B2 (en) | 2013-01-18 | 2018-08-21 | Basf Se | Acrylic dispersion-based coating compositions |
EP3569623B1 (en) * | 2017-01-16 | 2023-08-09 | Consejo Superior de Investigaciones Científicas (CSIC) | Vinyl-lactam-based hydrogel coatings |
Families Citing this family (87)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9056880B2 (en) | 2006-09-29 | 2015-06-16 | Johnson & Johnson Vision Care, Inc. | Process for producing hydrolysis-resistant silicone compounds |
US7838698B2 (en) | 2006-09-29 | 2010-11-23 | Johnson & Johnson Vision Care, Inc. | Hydrolysis-resistant silicone compounds |
US8242187B2 (en) * | 2006-09-29 | 2012-08-14 | Toray Industries, Inc. | Silicone polymer, ocular lenses, and contact lens |
CN101641615B (en) | 2007-03-22 | 2012-06-06 | 诺瓦提斯公司 | Silicone-containing prepolymers with dangling hydrophilic polymeric chains |
EP2175302B1 (en) | 2007-08-07 | 2018-09-19 | Nikon Corporation | Microscope |
US8119753B2 (en) * | 2007-10-23 | 2012-02-21 | Bausch & Lomb Incorporated | Silicone hydrogels with amino surface groups |
EP2238480B1 (en) | 2007-12-20 | 2012-02-01 | Novartis AG | Method for making contact lenses |
US7897654B2 (en) * | 2007-12-27 | 2011-03-01 | Johnson & Johnson Vision Care Inc. | Silicone prepolymer solutions |
US20090168013A1 (en) * | 2007-12-27 | 2009-07-02 | Kunzler Jay F | Trimethylsilyl-Capped Polysiloxane Macromonomers Containing Polar Fluorinated Side-Chains |
JP5398723B2 (en) * | 2008-02-06 | 2014-01-29 | ダイキン工業株式会社 | Fluorosilicone and fluorine-containing silicon-containing surface treatment agent |
US8079703B2 (en) | 2008-07-21 | 2011-12-20 | Novartis Ag | Silicone-containing polymeric materials with hydrolyzable groups |
US20130203812A1 (en) | 2008-09-30 | 2013-08-08 | Johnson & Johnson Vision Care, Inc. | Ionic silicone hydrogels comprising pharmaceutical and/or nutriceutical components and having improved hydrolytic stability |
US8470906B2 (en) * | 2008-09-30 | 2013-06-25 | Johnson & Johnson Vision Care, Inc. | Ionic silicone hydrogels having improved hydrolytic stability |
WO2010056687A2 (en) * | 2008-11-13 | 2010-05-20 | Novartis Ag | Silicone hydrogel materials with chemically bound wetting agents |
BRPI0921894A2 (en) * | 2008-11-13 | 2015-12-29 | Novartis Ag | polysiloxane copolymers with terminal hydrophilic polymer chains |
TWI506333B (en) * | 2008-12-05 | 2015-11-01 | Novartis Ag | Ophthalmic devices for delivery of hydrophobic comfort agents and preparation method thereof |
NZ592674A (en) * | 2008-12-18 | 2012-08-31 | Novartis Ag | Method for making silicone hydrogel contact lenses |
AU2009333223B2 (en) | 2008-12-30 | 2012-02-23 | Novartis Ag | Tri-functional UV-absorbing compounds and use thereof |
JP5575881B2 (en) * | 2009-05-22 | 2014-08-20 | ノバルティス アーゲー | Actinically crosslinkable siloxane-containing copolymer |
US8642712B2 (en) | 2009-05-22 | 2014-02-04 | Novartis Ag | Actinically-crosslinkable siloxane-containing copolymers |
US8083348B2 (en) * | 2009-06-16 | 2011-12-27 | Bausch & Lomb Incorporated | Biomedical devices |
EP2480927A4 (en) * | 2009-09-15 | 2018-01-17 | Novartis AG | Prepolymers suitable for making ultra-violet absorbing contact lenses |
US8883051B2 (en) * | 2009-12-07 | 2014-11-11 | Novartis Ag | Methods for increasing the ion permeability of contact lenses |
TWI483996B (en) | 2009-12-08 | 2015-05-11 | Novartis Ag | A silicone hydrogel lens with a covalently attached coating |
EP2513711B1 (en) * | 2009-12-14 | 2017-07-12 | Novartis AG | Methods for making silicone hydrogel lenses from water-based lens formulations |
JP5720103B2 (en) * | 2010-03-18 | 2015-05-20 | 東レ株式会社 | Silicone hydrogels, ophthalmic lenses and contact lenses |
US8480227B2 (en) | 2010-07-30 | 2013-07-09 | Novartis Ag | Silicone hydrogel lenses with water-rich surfaces |
EP2598937B1 (en) * | 2010-07-30 | 2016-06-29 | Novartis AG | Amphiphilic polysiloxane prepolymers and uses thereof |
EP2598936B1 (en) | 2010-07-30 | 2017-11-01 | Novartis AG | Method for making uv-absorbing ophthalmic lenses |
US8835525B2 (en) | 2010-10-06 | 2014-09-16 | Novartis Ag | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
JP5784131B2 (en) | 2010-10-06 | 2015-09-24 | ノバルティス アーゲー | Polymerizable chain-extended polysiloxane with pendant hydrophilic groups |
CA2808462C (en) | 2010-10-06 | 2016-01-12 | Novartis Ag | Water-processable silicone-containing prepolymers and uses thereof |
WO2012078457A1 (en) | 2010-12-06 | 2012-06-14 | Novartis Ag | Method for making silicone hydrogel contact lenses |
SG190708A1 (en) | 2010-12-13 | 2013-07-31 | Novartis Ag | Ophthalmic lenses modified with functional groups and methods of making thereof |
WO2012130956A1 (en) | 2011-04-01 | 2012-10-04 | Novartis Ag | Composition for forming a contact lens |
JP5990579B2 (en) | 2011-06-09 | 2016-09-14 | ノバルティス アーゲー | Silicone hydrogel lens with nanotextured surface |
CN103917899B (en) | 2011-10-12 | 2018-04-03 | 诺华股份有限公司 | By being coated with the method for preparing UV absorbability eye-use lens |
US8937110B2 (en) | 2011-12-23 | 2015-01-20 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogels having a structure formed via controlled reaction kinetics |
US8937111B2 (en) | 2011-12-23 | 2015-01-20 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogels comprising desirable water content and oxygen permeability |
US9140825B2 (en) | 2011-12-23 | 2015-09-22 | Johnson & Johnson Vision Care, Inc. | Ionic silicone hydrogels |
US9588258B2 (en) | 2011-12-23 | 2017-03-07 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogels formed from zero diluent reactive mixtures |
US9125808B2 (en) | 2011-12-23 | 2015-09-08 | Johnson & Johnson Vision Care, Inc. | Ionic silicone hydrogels |
US9156934B2 (en) | 2011-12-23 | 2015-10-13 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogels comprising n-vinyl amides and hydroxyalkyl (meth)acrylates or (meth)acrylamides |
TWI488892B (en) * | 2011-12-29 | 2015-06-21 | Pegavision Corp | Method of manufacturing hydrophilic silicone prepolymer |
CN104955878B (en) * | 2012-03-22 | 2018-08-17 | 莫门蒂夫性能材料股份有限公司 | The organosilicon polymer of organic group-modification |
CN104272142B (en) | 2012-03-22 | 2019-06-14 | 莫门蒂夫性能材料股份有限公司 | Hydrophilic macromonomer and hydrogel comprising the monomer |
US9395468B2 (en) | 2012-08-27 | 2016-07-19 | Ocular Dynamics, Llc | Contact lens with a hydrophilic layer |
US8937133B2 (en) | 2012-09-25 | 2015-01-20 | National Chiao Tung University | Dissoluble PDMS-modified p(HEMA-MAA) amphiphilic copolymer and method for fabricating the same |
BR112015006873A2 (en) * | 2012-09-27 | 2017-07-04 | Rhodia Operations | process to produce silver and copolymer nanostructures useful in such a process |
CN103819610B (en) * | 2012-11-16 | 2015-12-02 | 江南大学 | A kind of preparation method of pH responsive type inorganic polymer hybridized hydrogel |
US10338408B2 (en) | 2012-12-17 | 2019-07-02 | Novartis Ag | Method for making improved UV-absorbing ophthalmic lenses |
US20140268028A1 (en) * | 2013-03-15 | 2014-09-18 | Johnson & Johnson Vision Care, Inc. | Silicone-containing contact lens having clay treatment applied thereto |
JP2016524178A (en) * | 2013-04-30 | 2016-08-12 | クーパーヴィジョン インターナショナル ホウルディング カンパニー リミテッド パートナーシップ | Primary amine-containing silicone hydrogel contact lenses and related compositions and methods |
TWI610951B (en) * | 2013-09-10 | 2018-01-11 | 國立交通大學 | Organic-inorganic hybrid siloxane hydrogel composition manufacturing method |
SG11201601189RA (en) * | 2013-09-30 | 2016-04-28 | Novartis Ag | Silicone hydrogel lenses with relatively-long thermal stability |
US9568645B2 (en) | 2013-09-30 | 2017-02-14 | Novartis Ag | Silicone hydrogel lenses with relatively-long thermal stability |
WO2015048035A1 (en) | 2013-09-30 | 2015-04-02 | Novartis Ag | Method for making uv-absorbing ophthalmic lenses |
US9919456B2 (en) | 2013-10-31 | 2018-03-20 | Novartis Ag | Method for producing ophthalmic lenses |
WO2015073758A1 (en) | 2013-11-15 | 2015-05-21 | Ocular Dynamics, Llc | Contact lens with a hydrophilic layer |
EP3079888B1 (en) | 2013-12-13 | 2018-01-31 | Novartis AG | Method for making contact lenses |
US9708087B2 (en) | 2013-12-17 | 2017-07-18 | Novartis Ag | Silicone hydrogel lens with a crosslinked hydrophilic coating |
CN103951797B (en) * | 2014-03-17 | 2017-05-03 | 江苏诺飞新材料科技有限公司 | Organic silicon graft copolymer and its preparation method and application |
AU2015201321A1 (en) | 2014-03-31 | 2015-10-15 | Johnson & Johnson Vision Care, Inc. | Silicone acrylamide copolymer |
HUE046948T2 (en) | 2014-08-26 | 2020-03-30 | Novartis Ag | Method for applying stable coating on silicone hydrogel contact lenses |
WO2016048853A1 (en) * | 2014-09-26 | 2016-03-31 | Novartis Ag | Polymerizable polysiloxanes with hydrophilic substituents |
US10160141B2 (en) | 2014-11-25 | 2018-12-25 | Novartis Ag | Molds for making contact lenses |
EP3229851A4 (en) | 2014-12-09 | 2018-08-01 | Tangible Science LLC | Medical device coating with a biocompatible layer |
US9851472B2 (en) | 2015-03-27 | 2017-12-26 | Momentive Performance Materials Inc. | Silicone-based hydrophilic copolymer and hydrogel compositions comprising the same |
CN104945570B (en) * | 2015-07-03 | 2017-06-09 | 东南大学 | A kind of Silica hydrogel contact lens and its surface reversion processing method |
EP3325541A4 (en) * | 2015-07-23 | 2019-04-17 | The University of North Carolina at Chapel Hill | Solvent-free supersoft and superelastic materials |
US10793657B2 (en) * | 2015-10-28 | 2020-10-06 | Lg Hausys, Ltd. | Antifouling acrylic resin for additive |
MY184638A (en) | 2015-12-15 | 2021-04-13 | Alcon Inc | Method for applying stable coating on silicone hydrogel contact lenses |
CA3004158C (en) | 2015-12-15 | 2020-06-30 | Novartis Ag | Amphiphilic branched polydiorganosiloxane macromers |
US10268053B2 (en) | 2016-02-22 | 2019-04-23 | Novartis Ag | UV/visible-absorbing vinylic monomers and uses thereof |
WO2017145024A1 (en) | 2016-02-22 | 2017-08-31 | Novartis Ag | Uv-absorbing vinylic monomers and uses thereof |
JP6783931B2 (en) | 2016-10-26 | 2020-11-11 | アルコン インク. | Amphiphile branched chain polydiorganosiloxane macromer |
US10906258B2 (en) | 2017-08-29 | 2021-02-02 | Alcon Inc. | Cast-molding process for producing contact lenses |
EP3724698B1 (en) | 2017-12-13 | 2021-12-15 | Alcon Inc. | Method for producing mps-compatible water gradient contact lenses |
US11111327B2 (en) | 2018-01-22 | 2021-09-07 | Alcon Inc. | Cast-molding process for producing UV-absorbing contact lenses |
EP3890952B1 (en) | 2018-12-03 | 2023-07-05 | Alcon Inc. | Method for making coated silicone hydrogel contact lenses |
EP3890951B1 (en) | 2018-12-03 | 2023-06-07 | Alcon Inc. | Method for coated silicone hydrogel contact lenses |
EP3894200B1 (en) | 2018-12-14 | 2023-01-04 | Alcon Inc. | Method for making silicone hydrogel contact lenses |
SG11202108875UA (en) | 2019-04-10 | 2021-10-28 | Alcon Inc | Method for producing coated contact lenses |
WO2020240442A1 (en) | 2019-05-28 | 2020-12-03 | Alcon Inc. | Pad transfer printing instrument and method for making colored contact lenses |
TW202142576A (en) | 2020-01-27 | 2021-11-16 | 新加坡商科萊博新加坡私人有限公司 | Actinically-crosslinkable polysiloxane-polyglycerol block copolymers and methods of making and use thereof |
US20220365427A1 (en) * | 2021-04-30 | 2022-11-17 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist composition and method for manufacturing a semiconductor device |
CN116496501B (en) * | 2023-04-04 | 2024-03-29 | 浙江精一新材料科技有限公司 | Liquid polysiloxane with lactam group and light valve |
Citations (77)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4042552A (en) | 1972-09-19 | 1977-08-16 | Warner-Lambert Company | Composition for hydrophilic lens blank and method of casting |
US4045547A (en) | 1974-11-21 | 1977-08-30 | Warner-Lambert Company | Fabrication of soft contact lens and composition therefor |
US4136250A (en) * | 1977-07-20 | 1979-01-23 | Ciba-Geigy Corporation | Polysiloxane hydrogels |
US4229273A (en) * | 1977-03-31 | 1980-10-21 | Essilor International Compagnie Generale D'optique | Method for preparing silicone graft copolymers |
US4312575A (en) | 1979-09-18 | 1982-01-26 | Peyman Gholam A | Soft corneal contact lens with tightly cross-linked polymer coating and method of making same |
US4444711A (en) | 1981-12-21 | 1984-04-24 | Husky Injection Molding Systems Ltd. | Method of operating a two-shot injection-molding machine |
US4460534A (en) | 1982-09-07 | 1984-07-17 | International Business Machines Corporation | Two-shot injection molding |
US4543398A (en) * | 1983-04-28 | 1985-09-24 | Minnesota Mining And Manufacturing Company | Ophthalmic devices fabricated from urethane acrylates of polysiloxane alcohols |
US4632844A (en) | 1984-02-04 | 1986-12-30 | Japan Synthetic Rubber Co., Ltd. | Optical product having a thin film on the surface |
EP0216074A2 (en) * | 1985-07-31 | 1987-04-01 | Ciba-Geigy Ag | Polyvinyl alcohol derivatives and crosslinked hydrogel contact lenses made therefrom |
US4703097A (en) * | 1986-04-10 | 1987-10-27 | Bayer Aktiengesellschaft | Optical contact objects |
DE3710343A1 (en) * | 1987-03-28 | 1988-10-06 | Basf Lacke & Farben | BRANCHED ACRYLATE COPOLYMER WITH POLISHABLE DOUBLE BINDINGS AND METHOD FOR PRODUCING THE ACRYLATE COPOLYMER |
US4780515A (en) * | 1987-02-05 | 1988-10-25 | Bausch & Lomb Incorporated | Continuous-wear lenses having improved physical properties |
EP0331633A2 (en) * | 1988-02-26 | 1989-09-06 | Ciba-Geigy Ag | Hydrophilic modifier monomers |
US5036139A (en) | 1989-09-29 | 1991-07-30 | E. I. Du Pont De Nemours And Company | Hybrid acrylic star polymers with polysiloxane cores |
US5063139A (en) * | 1989-06-19 | 1991-11-05 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material capable of being processed at ultrahigh speed and process for the formation of color images using thereof |
US5070170A (en) * | 1988-02-26 | 1991-12-03 | Ciba-Geigy Corporation | Wettable, rigid gas permeable, substantially non-swellable contact lens containing block copolymer polysiloxane-polyoxyalkylene backbone units, and use thereof |
US5070215A (en) * | 1989-05-02 | 1991-12-03 | Bausch & Lomb Incorporated | Novel vinyl carbonate and vinyl carbamate contact lens material monomers |
US5070169A (en) * | 1988-02-26 | 1991-12-03 | Ciba-Geigy Corporation | Wettable, flexible, oxygen permeable contact lens containing block copolymer polysiloxane-polyoxyalkylene backbone units and use thereof |
WO1992009421A2 (en) * | 1990-11-27 | 1992-06-11 | Bausch & Lomb Incorporated | Mold materials for silicone containing lens materials |
WO1992018548A1 (en) * | 1991-04-18 | 1992-10-29 | Optical Research, Inc. | Novel composition for contact lenses |
US5198477A (en) | 1991-02-28 | 1993-03-30 | Ciba-Geigy Corporation | Contact lenses made from thermoformable material |
WO1993009084A1 (en) * | 1991-11-05 | 1993-05-13 | Bausch & Lomb Incorporated | Novel uv curable crosslinking agents useful in copolymerization |
US5219965A (en) * | 1990-11-27 | 1993-06-15 | Bausch & Lomb Incorporated | Surface modification of polymer objects |
US5244981A (en) * | 1990-04-10 | 1993-09-14 | Permeable Technologies, Inc. | Silicone-containing contact lens polymers, oxygen permeable contact lenses and methods for making these lenses and treating patients with visual impairment |
WO1993023773A1 (en) * | 1992-05-14 | 1993-11-25 | Ciba-Geigy Ag | Process for preparation of oxygen permeable polymer material |
US5314960A (en) * | 1990-04-10 | 1994-05-24 | Permeable Technologies, Inc. | Silicone-containing polymers, oxygen permeable hydrophilic contact lenses and methods for making these lenses and treating patients with visual impairment |
US5314961A (en) * | 1990-10-11 | 1994-05-24 | Permeable Technologies, Inc. | Silicone-containing polymers, compositions and improved oxygen permeable hydrophilic contact lenses |
US5336797A (en) * | 1992-12-30 | 1994-08-09 | Bausch & Lomb Incorporated | Siloxane macromonomers |
US5358995A (en) * | 1992-05-15 | 1994-10-25 | Bausch & Lomb Incorporated | Surface wettable silicone hydrogels |
US5387633A (en) * | 1994-03-08 | 1995-02-07 | W. R. Grace & Co.-Conn. | Styrene sodium styrene sulfonate copolymer for plastisol sealant |
US5505884A (en) * | 1988-05-31 | 1996-04-09 | Pilkington Barnes Hind Inc. | Contact lenses and materials and methods of making same |
US5508317A (en) | 1993-08-06 | 1996-04-16 | Ciba-Geigy Corporation | Photocrosslinked polymers |
US5527925A (en) | 1993-07-02 | 1996-06-18 | Ciba-Geigy Corporation | Functionalized photoinitiators, macromers thereof, and the use thereof |
US5665840A (en) * | 1994-11-18 | 1997-09-09 | Novartis Corporation | Polymeric networks from water-soluble prepolymers |
US5708094A (en) * | 1996-12-17 | 1998-01-13 | Bausch & Lomb Incorporated | Polybutadiene-based compositions for contact lenses |
US5712356A (en) | 1993-11-26 | 1998-01-27 | Ciba Vision Corporation | Cross-linkable copolymers and hydrogels |
US5760100A (en) * | 1994-09-06 | 1998-06-02 | Ciba Vision Corporation | Extended wear ophthalmic lens |
WO1998025982A1 (en) * | 1996-12-13 | 1998-06-18 | Novartis Ag | Porous polyorganosiloxane polymers |
US5807944A (en) * | 1996-06-27 | 1998-09-15 | Ciba Vision Corporation | Amphiphilic, segmented copolymer of controlled morphology and ophthalmic devices including contact lenses made therefrom |
US5843346A (en) | 1994-06-30 | 1998-12-01 | Polymer Technology Corporation | Method of cast molding contact lenses |
US5849841A (en) | 1995-02-03 | 1998-12-15 | Ciba Vision Corporation | Crosslinked polymers containing ester or amide groups |
US5894002A (en) | 1993-12-13 | 1999-04-13 | Ciba Vision Corporation | Process and apparatus for the manufacture of a contact lens |
US5981675A (en) * | 1998-12-07 | 1999-11-09 | Bausch & Lomb Incorporated | Silicone-containing macromonomers and low water materials |
US5981669A (en) * | 1997-12-29 | 1999-11-09 | Bausch & Lomb Incorporated | Silicone-containing prepolymers and low water materials |
US5998498A (en) * | 1998-03-02 | 1999-12-07 | Johnson & Johnson Vision Products, Inc. | Soft contact lenses |
US6039913A (en) * | 1998-08-27 | 2000-03-21 | Novartis Ag | Process for the manufacture of an ophthalmic molding |
WO2000031150A1 (en) | 1998-11-20 | 2000-06-02 | Novartis Ag | Functionalized polyallylamines and process for producing the same |
WO2000059970A1 (en) | 1999-03-30 | 2000-10-12 | Novartis Ag | Organic compounds |
US6165408A (en) | 1997-02-04 | 2000-12-26 | Novartis Ag | Moulded ophthalmic article |
US6221303B1 (en) | 1997-02-21 | 2001-04-24 | Novartis Ag | Ophthalmic mouldings |
EP0958315B1 (en) | 1997-02-04 | 2001-06-27 | Novartis AG | Moulded ophthalmic article |
EP0932635B1 (en) | 1996-10-21 | 2001-07-11 | Novartis AG | Crosslinkable polymers |
WO2001071392A1 (en) * | 2000-03-24 | 2001-09-27 | Novartis Ag | Crosslinkable or polymerizable prepolymers |
US6303687B1 (en) | 1995-02-03 | 2001-10-16 | Novartis Ag | Crosslinked polymers containing salt structures |
US6342570B1 (en) | 1994-11-14 | 2002-01-29 | Novartis Ag | Cross-linkable copolymers and hydrogels |
US6367929B1 (en) | 1998-03-02 | 2002-04-09 | Johnson & Johnson Vision Care, Inc. | Hydrogel with internal wetting agent |
US6444776B1 (en) * | 1998-12-21 | 2002-09-03 | Novartis Ag | Organic polymers |
US6451871B1 (en) | 1998-11-25 | 2002-09-17 | Novartis Ag | Methods of modifying surface characteristics |
US6479587B1 (en) | 1997-09-16 | 2002-11-12 | Novartis Ag | Crosslinkable polyurea polymers |
US6627124B1 (en) | 1997-10-21 | 2003-09-30 | Novartis Ag | Single mould alignment |
US6719929B2 (en) | 2000-02-04 | 2004-04-13 | Novartis Ag | Method for modifying a surface |
US20040082680A1 (en) | 2002-08-14 | 2004-04-29 | Phelan John Christopher | Radiation-curable prepolymers |
US6762264B2 (en) * | 1999-07-27 | 2004-07-13 | Bausch & Lomb Incorporated | Contact lens material |
US6765083B2 (en) * | 2000-11-03 | 2004-07-20 | Johnson & Johnson Vision Care, Inc. | Solvents useful in the preparation of polymers containing hydrophilic and hydrophobic monomers |
US6793973B2 (en) | 2000-02-04 | 2004-09-21 | Novartis Ag | Single-dip process for achieving a layer-by-layer-like coating |
US6811805B2 (en) | 2001-05-30 | 2004-11-02 | Novatis Ag | Method for applying a coating |
US6822016B2 (en) * | 2001-09-10 | 2004-11-23 | Johnson & Johnson Vision Care, Inc. | Biomedical devices containing internal wetting agents |
US6896926B2 (en) | 2002-09-11 | 2005-05-24 | Novartis Ag | Method for applying an LbL coating onto a medical device |
US20050113549A1 (en) | 2003-11-25 | 2005-05-26 | Devlin Brian G. | Crosslinkable polyurea prepolymers |
US6943203B2 (en) * | 1998-03-02 | 2005-09-13 | Johnson & Johnson Vision Care, Inc. | Soft contact lenses |
US20050237483A1 (en) * | 2004-04-21 | 2005-10-27 | Phelan John C | Curable colored inks for making colored silicone hydrogel lenses |
US7025131B2 (en) * | 2003-09-05 | 2006-04-11 | Baugh Benton F | Electrical tubing control and remediation apparatus and method of use |
US7160953B2 (en) * | 1991-07-05 | 2007-01-09 | Biocompatibles Uk Limited | Polymeric surface coatings |
US7249848B2 (en) * | 2004-09-30 | 2007-07-31 | Johnson & Johnson Vision Care, Inc. | Wettable hydrogels comprising reactive, hydrophilic, polymeric internal wetting agents |
US7279507B2 (en) | 1998-07-08 | 2007-10-09 | Coopervision International Holding Company, Lp | Contact lenses |
WO2007146137A2 (en) | 2006-06-08 | 2007-12-21 | Novartis Ag | Method for making silicone hydrogel contact lenses with good coating durability |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5196458A (en) * | 1991-10-15 | 1993-03-23 | Johnson & Johnson Vision Products, Inc. | Soft, high oxygen permeability ophthalmic lens |
TW393498B (en) * | 1995-04-04 | 2000-06-11 | Novartis Ag | The preparation and use of Polysiloxane-comprising perfluoroalkyl ethers |
US7052131B2 (en) | 2001-09-10 | 2006-05-30 | J&J Vision Care, Inc. | Biomedical devices containing internal wetting agents |
JP3771711B2 (en) * | 1998-03-31 | 2006-04-26 | 互応化学工業株式会社 | Method for producing photo solder resist ink |
JP2000034326A (en) | 1998-07-21 | 2000-02-02 | Shinnakamura Kagaku Kogyo Kk | Siloxane copolymer and its production |
-
2008
- 2008-03-21 WO PCT/US2008/057774 patent/WO2008116131A2/en active Application Filing
- 2008-03-21 AU AU2008228760A patent/AU2008228760B2/en not_active Ceased
- 2008-03-21 CN CN2008800091732A patent/CN101641206B/en not_active Expired - Fee Related
- 2008-03-21 CA CA2679322A patent/CA2679322C/en not_active Expired - Fee Related
- 2008-03-21 RU RU2009138706/05A patent/RU2462361C2/en not_active IP Right Cessation
- 2008-03-21 JP JP2009554757A patent/JP5484916B2/en not_active Expired - Fee Related
- 2008-03-21 KR KR1020097021987A patent/KR101482808B1/en not_active IP Right Cessation
- 2008-03-21 US US12/077,772 patent/US8071658B2/en active Active
- 2008-03-21 MX MX2009010116A patent/MX2009010116A/en active IP Right Grant
- 2008-03-21 BR BRPI0809271-0A2A patent/BRPI0809271A2/en not_active Application Discontinuation
- 2008-03-21 EP EP08744162.2A patent/EP2129513B1/en not_active Not-in-force
-
2009
- 2009-07-13 ZA ZA200904884A patent/ZA200904884B/en unknown
-
2011
- 2011-10-28 US US13/284,092 patent/US8263679B2/en active Active
Patent Citations (101)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4042552A (en) | 1972-09-19 | 1977-08-16 | Warner-Lambert Company | Composition for hydrophilic lens blank and method of casting |
US4045547A (en) | 1974-11-21 | 1977-08-30 | Warner-Lambert Company | Fabrication of soft contact lens and composition therefor |
US4229273A (en) * | 1977-03-31 | 1980-10-21 | Essilor International Compagnie Generale D'optique | Method for preparing silicone graft copolymers |
US4136250A (en) * | 1977-07-20 | 1979-01-23 | Ciba-Geigy Corporation | Polysiloxane hydrogels |
US4312575A (en) | 1979-09-18 | 1982-01-26 | Peyman Gholam A | Soft corneal contact lens with tightly cross-linked polymer coating and method of making same |
US4444711A (en) | 1981-12-21 | 1984-04-24 | Husky Injection Molding Systems Ltd. | Method of operating a two-shot injection-molding machine |
US4460534A (en) | 1982-09-07 | 1984-07-17 | International Business Machines Corporation | Two-shot injection molding |
US4543398A (en) * | 1983-04-28 | 1985-09-24 | Minnesota Mining And Manufacturing Company | Ophthalmic devices fabricated from urethane acrylates of polysiloxane alcohols |
US4632844A (en) | 1984-02-04 | 1986-12-30 | Japan Synthetic Rubber Co., Ltd. | Optical product having a thin film on the surface |
EP0216074A2 (en) * | 1985-07-31 | 1987-04-01 | Ciba-Geigy Ag | Polyvinyl alcohol derivatives and crosslinked hydrogel contact lenses made therefrom |
US4703097A (en) * | 1986-04-10 | 1987-10-27 | Bayer Aktiengesellschaft | Optical contact objects |
US4780515A (en) * | 1987-02-05 | 1988-10-25 | Bausch & Lomb Incorporated | Continuous-wear lenses having improved physical properties |
DE3710343A1 (en) * | 1987-03-28 | 1988-10-06 | Basf Lacke & Farben | BRANCHED ACRYLATE COPOLYMER WITH POLISHABLE DOUBLE BINDINGS AND METHOD FOR PRODUCING THE ACRYLATE COPOLYMER |
US5227432A (en) * | 1987-03-28 | 1993-07-13 | Basf Lacke & Farben Ag | Branched acrylate copolymer with polymerizable double bonds and methods for the production of the acrylate copolymer |
EP0331633A2 (en) * | 1988-02-26 | 1989-09-06 | Ciba-Geigy Ag | Hydrophilic modifier monomers |
US5070170A (en) * | 1988-02-26 | 1991-12-03 | Ciba-Geigy Corporation | Wettable, rigid gas permeable, substantially non-swellable contact lens containing block copolymer polysiloxane-polyoxyalkylene backbone units, and use thereof |
US5070169A (en) * | 1988-02-26 | 1991-12-03 | Ciba-Geigy Corporation | Wettable, flexible, oxygen permeable contact lens containing block copolymer polysiloxane-polyoxyalkylene backbone units and use thereof |
US5505884A (en) * | 1988-05-31 | 1996-04-09 | Pilkington Barnes Hind Inc. | Contact lenses and materials and methods of making same |
US5070215A (en) * | 1989-05-02 | 1991-12-03 | Bausch & Lomb Incorporated | Novel vinyl carbonate and vinyl carbamate contact lens material monomers |
US5063139A (en) * | 1989-06-19 | 1991-11-05 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material capable of being processed at ultrahigh speed and process for the formation of color images using thereof |
US5036139A (en) | 1989-09-29 | 1991-07-30 | E. I. Du Pont De Nemours And Company | Hybrid acrylic star polymers with polysiloxane cores |
US5331067A (en) * | 1990-04-10 | 1994-07-19 | Permeable Technologies, Inc. | Silicone-containing contact lens polymers, oxygen permeable contact lenses and methods for making these lenses and treating patients with visual impairment |
US5314960A (en) * | 1990-04-10 | 1994-05-24 | Permeable Technologies, Inc. | Silicone-containing polymers, oxygen permeable hydrophilic contact lenses and methods for making these lenses and treating patients with visual impairment |
US5244981A (en) * | 1990-04-10 | 1993-09-14 | Permeable Technologies, Inc. | Silicone-containing contact lens polymers, oxygen permeable contact lenses and methods for making these lenses and treating patients with visual impairment |
US5314961A (en) * | 1990-10-11 | 1994-05-24 | Permeable Technologies, Inc. | Silicone-containing polymers, compositions and improved oxygen permeable hydrophilic contact lenses |
US5219965A (en) * | 1990-11-27 | 1993-06-15 | Bausch & Lomb Incorporated | Surface modification of polymer objects |
WO1992009421A2 (en) * | 1990-11-27 | 1992-06-11 | Bausch & Lomb Incorporated | Mold materials for silicone containing lens materials |
US5158717A (en) * | 1990-11-27 | 1992-10-27 | Bausch & Lomb Incorporated | Method of molding shaped polymeric articles |
US5198477A (en) | 1991-02-28 | 1993-03-30 | Ciba-Geigy Corporation | Contact lenses made from thermoformable material |
WO1992018548A1 (en) * | 1991-04-18 | 1992-10-29 | Optical Research, Inc. | Novel composition for contact lenses |
US7160953B2 (en) * | 1991-07-05 | 2007-01-09 | Biocompatibles Uk Limited | Polymeric surface coatings |
US5310779A (en) * | 1991-11-05 | 1994-05-10 | Bausch & Lomb Incorporated | UV curable crosslinking agents useful in copolymerization |
WO1993009084A1 (en) * | 1991-11-05 | 1993-05-13 | Bausch & Lomb Incorporated | Novel uv curable crosslinking agents useful in copolymerization |
US5449729A (en) * | 1991-11-05 | 1995-09-12 | Bausch & Lomb Incorporated | UV curable crosslinking agents useful in copolymerization |
WO1993023773A1 (en) * | 1992-05-14 | 1993-11-25 | Ciba-Geigy Ag | Process for preparation of oxygen permeable polymer material |
US5358995A (en) * | 1992-05-15 | 1994-10-25 | Bausch & Lomb Incorporated | Surface wettable silicone hydrogels |
US5336797A (en) * | 1992-12-30 | 1994-08-09 | Bausch & Lomb Incorporated | Siloxane macromonomers |
US5563184A (en) * | 1992-12-30 | 1996-10-08 | Bausch & Lomb Incorporated | Macromonomers |
US5612389A (en) | 1993-07-02 | 1997-03-18 | Ciba Geigy Corporation | Functionalized photoinitiators, macromers thereof, and the use thereof |
US5527925A (en) | 1993-07-02 | 1996-06-18 | Ciba-Geigy Corporation | Functionalized photoinitiators, macromers thereof, and the use thereof |
US5621018A (en) | 1993-07-02 | 1997-04-15 | Ciba Geigy Corporation | Functionalized photoinitiators, macromers thereof, and the use thereof |
US5612391A (en) | 1993-07-02 | 1997-03-18 | Ciba Geigy Corporation | Functionalized photoinitiators, macromers thereof, and the use thereof for contact lens |
US5583163A (en) | 1993-08-06 | 1996-12-10 | Ciba Geigy Corporation | Photocrosslinked polymers |
US5508317A (en) | 1993-08-06 | 1996-04-16 | Ciba-Geigy Corporation | Photocrosslinked polymers |
US5849810A (en) | 1993-08-06 | 1998-12-15 | Ciba Vision Corporation | Photocrosslinked polymers |
US5789464A (en) | 1993-08-06 | 1998-08-04 | Ciba Vision Corporation | Photocrosslinked polymers |
US5936052A (en) | 1993-11-26 | 1999-08-10 | Ciba Vision Corporation | Cross-linkable copolymers and hydrogels |
US5712356A (en) | 1993-11-26 | 1998-01-27 | Ciba Vision Corporation | Cross-linkable copolymers and hydrogels |
US5894002A (en) | 1993-12-13 | 1999-04-13 | Ciba Vision Corporation | Process and apparatus for the manufacture of a contact lens |
US5387633A (en) * | 1994-03-08 | 1995-02-07 | W. R. Grace & Co.-Conn. | Styrene sodium styrene sulfonate copolymer for plastisol sealant |
US5843346A (en) | 1994-06-30 | 1998-12-01 | Polymer Technology Corporation | Method of cast molding contact lenses |
US5760100B1 (en) * | 1994-09-06 | 2000-11-14 | Ciba Vision Corp | Extended wear ophthalmic lens |
US5849811A (en) | 1994-09-06 | 1998-12-15 | Ciba Vision Corporation | Extended wear ophthalmic lens |
US5760100A (en) * | 1994-09-06 | 1998-06-02 | Ciba Vision Corporation | Extended wear ophthalmic lens |
US5849811B1 (en) | 1994-09-06 | 2000-11-14 | Ciba Vision Corporatin | Extended wear ophthalmic lens |
US6342570B1 (en) | 1994-11-14 | 2002-01-29 | Novartis Ag | Cross-linkable copolymers and hydrogels |
US5665840A (en) * | 1994-11-18 | 1997-09-09 | Novartis Corporation | Polymeric networks from water-soluble prepolymers |
US5849841A (en) | 1995-02-03 | 1998-12-15 | Ciba Vision Corporation | Crosslinked polymers containing ester or amide groups |
US6303687B1 (en) | 1995-02-03 | 2001-10-16 | Novartis Ag | Crosslinked polymers containing salt structures |
US5807944A (en) * | 1996-06-27 | 1998-09-15 | Ciba Vision Corporation | Amphiphilic, segmented copolymer of controlled morphology and ophthalmic devices including contact lenses made therefrom |
EP0932635B1 (en) | 1996-10-21 | 2001-07-11 | Novartis AG | Crosslinkable polymers |
US6492478B1 (en) | 1996-10-21 | 2002-12-10 | Novartis Ag | Polymers with crosslinkable pendent groups |
WO1998025982A1 (en) * | 1996-12-13 | 1998-06-18 | Novartis Ag | Porous polyorganosiloxane polymers |
US5708094A (en) * | 1996-12-17 | 1998-01-13 | Bausch & Lomb Incorporated | Polybutadiene-based compositions for contact lenses |
US6165408A (en) | 1997-02-04 | 2000-12-26 | Novartis Ag | Moulded ophthalmic article |
EP0958315B1 (en) | 1997-02-04 | 2001-06-27 | Novartis AG | Moulded ophthalmic article |
EP0961941B1 (en) | 1997-02-21 | 2002-04-17 | Novartis AG | Ophthalmic mouldings |
US6221303B1 (en) | 1997-02-21 | 2001-04-24 | Novartis Ag | Ophthalmic mouldings |
US6479587B1 (en) | 1997-09-16 | 2002-11-12 | Novartis Ag | Crosslinkable polyurea polymers |
US6627124B1 (en) | 1997-10-21 | 2003-09-30 | Novartis Ag | Single mould alignment |
US5981669A (en) * | 1997-12-29 | 1999-11-09 | Bausch & Lomb Incorporated | Silicone-containing prepolymers and low water materials |
US6943203B2 (en) * | 1998-03-02 | 2005-09-13 | Johnson & Johnson Vision Care, Inc. | Soft contact lenses |
US6367929B1 (en) | 1998-03-02 | 2002-04-09 | Johnson & Johnson Vision Care, Inc. | Hydrogel with internal wetting agent |
US5998498A (en) * | 1998-03-02 | 1999-12-07 | Johnson & Johnson Vision Products, Inc. | Soft contact lenses |
US7279507B2 (en) | 1998-07-08 | 2007-10-09 | Coopervision International Holding Company, Lp | Contact lenses |
US6039913A (en) * | 1998-08-27 | 2000-03-21 | Novartis Ag | Process for the manufacture of an ophthalmic molding |
WO2000031150A1 (en) | 1998-11-20 | 2000-06-02 | Novartis Ag | Functionalized polyallylamines and process for producing the same |
US6472489B1 (en) | 1998-11-20 | 2002-10-29 | Novartis Ag | Polymers |
US6451871B1 (en) | 1998-11-25 | 2002-09-17 | Novartis Ag | Methods of modifying surface characteristics |
US5981675A (en) * | 1998-12-07 | 1999-11-09 | Bausch & Lomb Incorporated | Silicone-containing macromonomers and low water materials |
US6444776B1 (en) * | 1998-12-21 | 2002-09-03 | Novartis Ag | Organic polymers |
WO2000059970A1 (en) | 1999-03-30 | 2000-10-12 | Novartis Ag | Organic compounds |
US6762264B2 (en) * | 1999-07-27 | 2004-07-13 | Bausch & Lomb Incorporated | Contact lens material |
US6719929B2 (en) | 2000-02-04 | 2004-04-13 | Novartis Ag | Method for modifying a surface |
US6793973B2 (en) | 2000-02-04 | 2004-09-21 | Novartis Ag | Single-dip process for achieving a layer-by-layer-like coating |
US7091283B2 (en) * | 2000-03-24 | 2006-08-15 | Novartis Ag | Crosslinkable prepolymers from a hydrophilic monomer and a hydrophobic crosslinker |
US20010037001A1 (en) * | 2000-03-24 | 2001-11-01 | Beat Muller | Novel polymers |
US7566754B2 (en) * | 2000-03-24 | 2009-07-28 | Novartis Ag | Process for making contact lenses from prepolymers |
US7268189B2 (en) * | 2000-03-24 | 2007-09-11 | Novartis Ag | Polymers |
US7238750B2 (en) * | 2000-03-24 | 2007-07-03 | Novartis Ag | Polymers |
WO2001071392A1 (en) * | 2000-03-24 | 2001-09-27 | Novartis Ag | Crosslinkable or polymerizable prepolymers |
US6765083B2 (en) * | 2000-11-03 | 2004-07-20 | Johnson & Johnson Vision Care, Inc. | Solvents useful in the preparation of polymers containing hydrophilic and hydrophobic monomers |
US6811805B2 (en) | 2001-05-30 | 2004-11-02 | Novatis Ag | Method for applying a coating |
US6822016B2 (en) * | 2001-09-10 | 2004-11-23 | Johnson & Johnson Vision Care, Inc. | Biomedical devices containing internal wetting agents |
US20040082680A1 (en) | 2002-08-14 | 2004-04-29 | Phelan John Christopher | Radiation-curable prepolymers |
US6896926B2 (en) | 2002-09-11 | 2005-05-24 | Novartis Ag | Method for applying an LbL coating onto a medical device |
US7025131B2 (en) * | 2003-09-05 | 2006-04-11 | Baugh Benton F | Electrical tubing control and remediation apparatus and method of use |
US20050113549A1 (en) | 2003-11-25 | 2005-05-26 | Devlin Brian G. | Crosslinkable polyurea prepolymers |
US20050237483A1 (en) * | 2004-04-21 | 2005-10-27 | Phelan John C | Curable colored inks for making colored silicone hydrogel lenses |
US7249848B2 (en) * | 2004-09-30 | 2007-07-31 | Johnson & Johnson Vision Care, Inc. | Wettable hydrogels comprising reactive, hydrophilic, polymeric internal wetting agents |
WO2007146137A2 (en) | 2006-06-08 | 2007-12-21 | Novartis Ag | Method for making silicone hydrogel contact lenses with good coating durability |
Non-Patent Citations (1)
Title |
---|
Response on Australian Office Action #2008228760 Dated: Aug. 16, 2010. |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9096025B2 (en) | 2008-07-21 | 2015-08-04 | Novartis Ag | Silicone hydrogel lenses with convertible comfort agents |
US9268064B2 (en) | 2012-12-14 | 2016-02-23 | Novartis Ag | Amphiphilic siloxane-containing (meth)acrylamides and uses thereof |
US9567352B2 (en) | 2012-12-14 | 2017-02-14 | Novartis Ag | Tris(trimethyl siloxy)silane vinylic monomers and uses thereof |
WO2014093756A1 (en) | 2012-12-14 | 2014-06-19 | Novartis Ag | Actinically-crosslinkable amphiphilic prepolymers |
US9097840B2 (en) | 2012-12-14 | 2015-08-04 | Novartis Ag | Amphiphilic siloxane-containing (meth)acrylamides and uses thereof |
WO2014093751A2 (en) | 2012-12-14 | 2014-06-19 | Novartis Ag | Amphiphilic siloxane-containing vinylic monomers and uses thereof |
US9151873B2 (en) | 2012-12-14 | 2015-10-06 | Novartis Ag | Actinically-crosslinkable amphiphilic prepolymers |
WO2014093764A1 (en) | 2012-12-14 | 2014-06-19 | Novartis Ag | Amphiphilic siloxane-containing (meth)acrylamides and uses thereof |
US9103965B2 (en) | 2012-12-14 | 2015-08-11 | Novartis Ag | Amphiphilic siloxane-containing vinylic monomers and uses thereof |
US9475827B2 (en) | 2012-12-14 | 2016-10-25 | Shin-Etsu Chemical Company, Ltd. | Tris(trimethyl siloxyl)silane vinylic monomers and uses thereof |
US9500775B2 (en) | 2012-12-14 | 2016-11-22 | Novartis Ag | Actinically-crosslinkable amphiphilic prepolymers |
US9541676B2 (en) | 2012-12-14 | 2017-01-10 | Novartis Ag | Amphiphilic siloxane-containing vinylic monomers and uses thereof |
US10053597B2 (en) | 2013-01-18 | 2018-08-21 | Basf Se | Acrylic dispersion-based coating compositions |
US9329306B2 (en) | 2014-04-25 | 2016-05-03 | Novartis Ag | Carbosiloxane vinylic monomers |
US9684095B2 (en) | 2014-04-25 | 2017-06-20 | Novartis Ag | Hydrophilized carbosiloxane vinylic monomers |
WO2015164630A1 (en) | 2014-04-25 | 2015-10-29 | Novartis Ag | Carbosiloxane vinylic monomers |
EP3569623B1 (en) * | 2017-01-16 | 2023-08-09 | Consejo Superior de Investigaciones Científicas (CSIC) | Vinyl-lactam-based hydrogel coatings |
Also Published As
Publication number | Publication date |
---|---|
EP2129513A2 (en) | 2009-12-09 |
US20080231798A1 (en) | 2008-09-25 |
ZA200904884B (en) | 2010-09-29 |
CA2679322C (en) | 2015-02-10 |
AU2008228760B2 (en) | 2010-09-23 |
JP2010522265A (en) | 2010-07-01 |
CN101641206B (en) | 2013-03-20 |
US20120046382A1 (en) | 2012-02-23 |
KR20100015770A (en) | 2010-02-12 |
WO2008116131A3 (en) | 2009-05-14 |
CN101641206A (en) | 2010-02-03 |
US8071658B2 (en) | 2011-12-06 |
EP2129513B1 (en) | 2016-08-03 |
BRPI0809271A2 (en) | 2014-10-14 |
RU2009138706A (en) | 2011-04-27 |
RU2462361C2 (en) | 2012-09-27 |
KR101482808B1 (en) | 2015-01-14 |
AU2008228760A1 (en) | 2008-09-25 |
MX2009010116A (en) | 2009-10-12 |
WO2008116131A2 (en) | 2008-09-25 |
JP5484916B2 (en) | 2014-05-07 |
CA2679322A1 (en) | 2008-09-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8263679B2 (en) | Prepolymers with dangling polysiloxane-containing polymer chains | |
US8071703B2 (en) | Silicone-containing prepolymers with dangling hydrophilic polymer chains | |
US8404759B2 (en) | Silicone hydrogel materials with chemically bound wetting agents | |
US8048968B2 (en) | Polysiloxane copolymers with terminal hydrophilic polymer chains | |
US8883928B2 (en) | Silicone-containing polymeric materials with hydrolyzable groups | |
US8383744B2 (en) | Actinically-crosslinkable siloxane-containing copolymers | |
US8357760B2 (en) | Silicone hydrogel contact lenses with convertible comfort agents |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: NOVARTIS AG, SWITZERLAND Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ZHOU, JIAN S.;SMITH, DAWN A.;SIGNING DATES FROM 20080321 TO 20080324;REEL/FRAME:027159/0562 |
|
FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
AS | Assignment |
Owner name: ALCON INC., SWITZERLAND Free format text: CONFIRMATORY DEED OF ASSIGNMENT EFFECTIVE APRIL 8, 2019;ASSIGNOR:NOVARTIS AG;REEL/FRAME:051454/0788 Effective date: 20191111 |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 8TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1552); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 8 |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 12TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1553); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 12 |